Last reviewed on May 11, 2015   —  233 Comments

Applies to Microsoft Outlook 2013, Outlook 2010, Outlook 2007, Outlook 2003 and below

There are several reasons why Microsoft Outlook won’t send mail and before you can fix the problem, you need to identify the cause.

Possibly the most common cause is the message is too large to send because you added a huge attachment to a message. If this is the problem, see Delete large messages from the Outbox if you can’t delete the stuck message. Instructions for Outlook 2011 for Mac are at Delete Messages Stuck in Outlook 2011 Outbox.

If you are using iCloud and messages get stuck, see Outlook and iCloud 2: What you need to know for the latest information.

If you are using a Comcast account and messages aren’t sending, you need to change your outgoing server to use port 587 or 465 and set Use this following type of encrypted connection to None then click OK.

If you don’t see a message in your outbox but Outlook is trying to send something, see Hidden Stuck Messages. It’s most likely a read receipt that won’t send.

If the message is not too large to send, other possible causes include:

  1. An add-in that marks items read if you view the Outbox
  2. Wrong password or not authenticating properly with the mail server
  3. Outlook or the mail server is offline
  4. No default email account is set
  5. Corrupt Send and Receive Settings
  6. Using a program that accesses pst or ost data, such as Desktop Search, Lync, etc
  7. An antispam or antivirus scanner is scanning outgoing mail

Troubleshooting

First, check the Send/Receive progress dialog for error codes. Browse to Tools, Send/Receive, Send/Receive settings, Show progress and click on the error tab. The error will resemble this, with a different error number and possibly a better explanation than “unknown error”

Task ‘<account> – Sending’ reported error (0x80040119) : ‘Unknown Error 0x80040119

See What does this error mean? for the reasons for some of the error codes. (If you need the text of the error code, you can select any error and use Ctrl+C to copy it.)

An add-in marks items read if you view the Outbox

Symptom: you look at the mail in the Outbox and it’s not bolded.
Quick Fix: Stop looking in the Outbox.
See Outlook: After viewing the Outbox, e-mail won’t send for applications that cause messages in the Outbox to be marked as read.

Wrong or bad password, or not authenticating properly with the mail server

Verify your password works by logging into your account using web access.

Check your account settings:

  1. Go to Tools menu (Outlook 2007) or File tab (Outlook 2010) then Account Settings, Email.
  2. Double click on the account then click More Settings.
  3. Check your settings on the Outgoing server tab. Many email providers now require a password to send email. If you aren’t sure, enabling authentication before sending usually doesn’t cause problems, but you should verify the proper settings with your email provider.
  4. Do not enable SPA unless your mail server requires it.
  5. Verify the port number is correct on the More Settings, Advanced tab. Many email providers use port 587 for SMTP.

In Outlook 2003 and older, go to Tools, E-mail accounts, View or Change existing accounts. Double click on the account and click More Settings, then select the Advanced tab.

Outlook or the mail server is offline

Is Outlook online? The online status is in the Status bar.

Is the mail server online? Outlook’s status bar may say ‘Trying to Connect’ if the mail server is down.

No default email account is set

Symptoms include being able to reply but not send new mail.
This may happen when you use a preconfigured script provided by the mail server administrator to set up your account.
In Outlook 2010, go to File, Account Settings, Email. Is an set as default?
In Outlook 007, you’ll check for a default account in Tools, Account Settings, Email. In Outlook 2003 and older, go to Tools, E-mail accounts, View or Change existing accounts. Verify an account is set as default.

The SRS file is corrupt

Outlook saves your Send and Receive customizations in a file with the extension *.SRS. If this file is corrupt, the Send & Receive Settings dialog won’t open and you may receive send & receive errors. Find and delete or rename the SRS file for your profile.

In Windows 7, 8 and Vista the SRS file is at C:\Users\username\AppData\Roaming\Microsoft\Outlook\. In Windows XP, the SRS file is found at C:\Documents and Settings\%username%\Application Data\Microsoft\Outlook\. In either case, you can type or paste %appdata%\microsoft\outlook in the address bar of Windows Explorer, then press Enter, to jump to the folder.

Using a program that accesses the .pst or .ost data

Symptom: Mail sends at first, then hangs in mailbox
Send and Receive error code is: Task ‘<account> – Sending’ reported error (0x80040119) : ‘Unknown Error 0x80040119.

Solutions include:

Use Scanpst to repair the pst file, or delete the ost file and let Outlook rebuild it. See Error message when you try to read or to delete email or when you click “Send/Receive” in Outlook: “An unknown error has occurred” or “Messaging interface has caused an unknown error” (MSKB) for more information.

Restarting Outlook (after verifying it closed completely in Task manager) may allow the mail to send.

Otherwise:

Reboot and disable the problem program before starting Outlook.

If it continues to cause problems (such as sending works for awhile after restarting Outlook, then stops), uninstall the software.

An antispam or antivirus scanner is scanning outgoing mail

Norton and AVG antispam plugins are known to cause problems, but there are others. Any antivirus that uses an Outlook addin can cause issues with your email.

Solution: Disable Email scanning in the software.

It may help to the timeout (in your email account’s More Settings, Advanced tab.) Otherwise, check your antispam or antivirus program’s website for an update or possible workarounds. Note that we do not recommend scanning email for viruses as any virus will be picked up if you try to open an infected message (which you know not to do :)).

If none of the above are the cause and the account settings look okay, turn on SMTP logging.

To turn on logging in Outlook 2010, go to File, Options, Advanced. Enable Troubleshooting logging is near the bottom, in the Other section. I n Outlook 2007 and Outlook 2003, go to Tools, Options, Other, Advanced and add a check to the box beside Enable Logging (troubleshooting).

Because logging can cause Outlook to be unstable, initiate a send and receive and once you’ve reproduced the error, disable logging. The log files are stored in your temp folder. Type %temp% in the address bar of Windows Explorer and press Enter to open the Temp folder. The log files will have the extension .log and may be in an Outlook Logging subfolder.

How to enable transport logging in Outlook (MSKB)

Hidden Messages that won’t Send

When you have a hidden message that won’t send, it’s a stuck read receipt. They are stored as hidden messages at the root level of your mailbox.

There are two methods that can be used to delete them:

1. Change the SMTP server for the account to a SMTP that can send the receipt. After the read receipt is sent, change the SMTP back to the one you normally use for the account after they are sent.

2. Delete the hidden messages using MFCMAPI or OutlookSpy. Because MFCMAPI does not need to be installed, it’s our choice for most users. (We do not recommend using MDBVue as it is out-dated and was replaced by MFCMAPI.)

We have complete instructions for deleting stuck read receipts using MFCMAPI at Delete Read Receipts using MFCMAPI.


Comments

  1. Frank Young says

    Outlook 2012 installed: send email with attachment and copy stays in Outbox but does send to recipient. Also keeps sending but will not leave outbox. I have to delete the email myself.

    • Diane Poremsky says

      How large is the message? Is it too large to send? Are you using an antivirus scanner that scans outlook email?

  2. Scott Kalkwarf says

    My wife just got a MAC and we are still learning. I've installed Office 2010. I'm having problems with a few emails not going out. Everything else will send and receive but these emails remain in the outbox. The first email has a whole bunch of emails to be sent to and is a txt only email. (there is a question mark at the front of the list, which is a yellow color, which I presume means that at least one email is incorrect) Would this stop it from sending? The second email has a list of 20 emails to be sent to. There is an attachment but it is only 50 kb so I wouldn't think that the attachment is too large. there is no question marks and the emails will highlight in blue when the cursor is on one. I appreciate your advice. My wife is so frustrated learning the MAC that she hates it right now.

  3. Steve says

    Diane:

    Hope you can help with a home PC issue.
    Machine is a W7HP with Office 2007 - has all MS patches etc,
    It is wired into my router - ISP is Verizon (never installed any of their software)
    I created a new profile (for a new job) according to the instruction:
    POP3
    Typed in proper out and in servers with UN and PW
    No instruction for SPA or use same settings
    No matter what variant of boxes I selected or checked, I cannot send mail - receiving is random.
    My wireless netbook exhibits same behavior, and when my iPhone is on my network, it fails as well

    Regular "Outlook" profile works fine (hits G-Mail and Hotmail fine)

    I'm guessing I need a port or have some other conflict

    Any guidance would be great

    Thanks

    • Diane Poremsky says

      what is the outgoing port #? If the mailbox is not on verizon, they may block access to the mailbox on pot 25. This wouldn't affect incoming mail though, only outgoing.

  4. sandip says

    i ve set mail id in MS-outlook express 2007 as me@domain.com,bt mail sent properly also go in sent box, bt mail not get at destination mai ID___ bt incoming mail get at inbox time to time ___
    please help me,
    thanks and regards
    sandy gupta

  5. Jay says

    Occasionally when I send a message, my own email address is included in the list of recipients (this can occur if a thread is bouncing back and forth and my own originating email address ends up as a recipient when replied to by someone else. If I then "reply all" I'm now sending to my own email address.)

    When this occurs, Outlook will not send the message - it freezes the send (to everyone) and I simply get a send/receive error. If the offending email is at the front of the queue, all subsequent email also get stuck. If I'm not carefully watching I won't notice this until some long time later, after wondering why the recipients have not responded.

    OK - I don't really care "why" this happens. But would like to resolve it as easily as possible.

    What's the easiest fix (besides paying more attention every time I hit "send")? Is there a way to restrict Outlook's recipient list so that it CAN'T (and won't try to) send messages to specific email addresses - such as my own? Othe ideas

    • Diane Poremsky says

      What type of email account do you use in Outlook? What antivirus? I'm wondering if its related to the smtp server you use or possibly antivirus/antispam scanner. I'll try to repro it - it's definitely should work on Outlook's end.

      Oh, and see if it works if you use Safe mode. (Close Outlook Hold Ctrl as you click on the Outlook icon - you'll get a dialog asking/telling you that it will start in Safe mode.)

  6. Jay says

    Regarding "send to own email address" problem referenced above, failed to indicate I'm using Office 2010 with Outlook v. 14.0.5xxx with XP

  7. Ken says

    I have a problem with Outlook 2010, I am using a Go Daddy email account. I have set up Outlook using their auto installer and i have done it manually. My ISP is Verizon, I have talked to Verizon support and Go Daddy support and have researched till my fingers bleed(haha not really). I have tried many different out going ports different versions of outlook, from different computers. The tests come back pass with both Go Daddy and Verizon servers, Still ending with I can receive but not send. I tried shutting down Norton and McAfee. If anyone has any ideas i would greatly appreciate it.

  8. Ken says

    the error message reads Sending' reported error (0x8004010F): An object cannot be found. The ports i have tried along with Verizon and go daddy support have been 25, 80, 3535. i believe there were a few more. I have also tried using Verizon's out going server under there instruction set up by their support. I have tried all those things in that link at least twice. Go daddy says its not their problem and Verizon says its go daddy's.

  9. sk manjur akter says

    Task 'skichlu@domain.com - Sending' reported error (0x800CCC78) : 'Cannot send the message. Verify the e-mail address in your account properties. The server responded: 550 Access denied - Invalid HELO name (See RFC2821 4.1.1.1)'

    • Diane Poremsky says

      What type of email account? We usually see this error when you are properly authenticating with the server. It's denying access because it doesn't "know" you.

      Open Account Settings, double click on the affected account then click More Settings. Check the Outgoing Server tab - are the settings correct? In most cases, you'll use same settings as incoming mail server. Next, check the Advanced tab. Are you using the correct security setting - try Auto if your version of Outlook supports it.

    • Diane Poremsky says

      Sorry, I was out of town and forgot to answer... An object can't be found error often refers to the address book object, not the SMTP servers... which makes it outlook's fault, not either VZ or GoDaddy. It's also more common with Exchange mailboxes, but being that you tried different ports, it means you aren't using exchange.

      What antivirus do you use? Symantec is known to cause this error.
      Did you try Safe mode? Safe mode will generally prevent addins and antivirus from interfering with outlook - if the error goes away we know its one or the other. (Close Outlook. Hold Ctrl as you click on the Outlook icon to start in Safe mode.)

  10. Sara Harms says

    Diane-
    We have been having problems with this account not sending emails. All are small, some without attachments and still sitting in outbox. Not sure what to do from here, as this doesn't always occur. Just sometimes it gets bogged down and you have to delete the sent messages, then resend each one individually, which may take an hour or so. Can you help?

  11. Mark says

    Hi guys,
    I'm running Outlook 03. I cannot send any emails. I have 3 other computers with the same email and same settings with regards to Ports. They have no problems. When I run a test email I get this message;
    "The specified server was found but there was no response from the server. Please verify that the port and SSL information is correct."
    The information is the same on all computers and this is the only one that doesn't work. I can receive emails.

    Any suggestions?

  12. Jim Wynne says

    Cannot delete mail in Outllok. Receiving the following message:

    User\jim\appdata\local\microsoft\outlook\outlook.pst is in use and cannot be accessed. Close any application that is using this file and try again. You might need to restart your computer.

  13. Barry says

    My emails get stuck in the outbook. If I open the stuck email and delete old parts of the "thread", then email will be sent. It's as if there is a size restriction on how large an outgoing email can be.

    I know that there is a size limitation on incoming emails and we increased that from the default size of 5 MB to 15MB. How do we change the size limitation in outlook for outbound emails??

  14. John says

    Just had my broadband email service updated and upgraded bt BT to make use of the backoffice365 features. Not a request from me but part of global BT upgrde program. Now i cannot send emails. BT have accepted there is a problem an escalated it ti microsoft who have still not solved the issue. Fyi using office outlook 2003.

    Would really appriciate some help on this.

    • Diane Poremsky says

      Is backoffice365 the same as Microsoft's Office 365 service, ie hosted Exchange? Do you get any error messages?

  15. John says

    Sorry for the confusion. It is the office 365 service. No error messages. Emails sit in the out box and will not send. BT IT engineers have had access to my PC and confirm that all settngs are correct. thisnis why they have escaleted it to Microsoft. its been over 2 weeks now and no sollution. i cannot believe i am the only one to have this problem.

    Outlook 2003 is SP3 and fully uptodate.

    • Diane Poremsky says

      Does it work if you use Safe mode? To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

      Because you are connecting to Office 365, it should "just work". There is nothing to screw up in when configuring Outlook for Office 365. It connects using port 80, so firewalls won't block it. Antivirus can interfere - Safe mode will help us know if that might be the problem.

  16. Vanessa says

    I'm having an issue with Microsoft Outlook calendars on my iPhone. Sometimes, when I accept or decline a calendar appointment, my phone keeps sending the same email receipt to the organizer every few seconds! Today I've sent over a thousand to two people; they're not happy, and neither am I. Unsure of how to stop it, I've disabled my WiFi and 3G networks. It's only happened once before today, about 3 months ago, but I normally have no problems.
    iPhone is the iPhone 4, Outlook/Exchange is through my employer. Encryption is enabled. I also receive my AOL email through my phone (don't know if you need to know that, but thought it might help). I emailed our IS department as well, but haven't gotten an answer yet. Thanks for any help you can give me.

  17. JohnB27 says

    A most unusual problem: MS Outlook 2003 using XP SP3 When Outlook starts it behaves as expected and downloads all incoming mail. Any email for which a reply is required is processed as an outgoing message with no problem and is sent.

    An example is an exchange of emails with a Contact that features in my Address Book.

    However if I decide to Compose and send a new email to that same contact the message is locked into the Outbox. The successful and failed messages have identical addresses in the Sender box!

    So I am restricted to replying to messages but not composing new ones!

    • Diane Poremsky says

      Are all new messages affected or just some?

      How are you addressing the new message? If the address comes up as you begin to type it, select it using the arrow keys then press delete. Retype the name and let it resolve or select the name using the To button. Does it work now? If this fixes it, the autocomplete cache either has a bad address or is corrupt.

      If all new messages are affected, it's corrupt. To remove the autocomplete cache in Outlook 2003, close outlook and paste %USERPROFILE%\Application Data\Microsoft\Outlook in the address bar of windows explorer. Locate the NK2 file for your profile and rename or delete it.

  18. Michael Jaffarian says

    I like to write an email, hit send and then have it go to the outbox and sit there until I hit send/receive all. I don't like to write it, hit send, and have it immediately go out there. I just can't find this setting. Thanks much.

    • Diane Poremsky says

      You have send immediately enabled in Options. Assuming Outlook 2010, File, Options, Advanced - about halfway down.

  19. Sharon says

    I can not send messages from my add on gmail acct. I get a message not connected to network, but everything is done as suggested. I have outlook 7

  20. Anis says

    Since many days, I am facing problems in my Outlook 2010 version- Mails stay in the OUTBOX when the LAN is hard wired to the PC. However, the emails get SENT when connected thru Wi-Fi. Can someone help this out

    • Diane Poremsky says

      Is it the same internet provider supplying wired and wireless? Check your authentication in File, Account Settings, double click on the account then More Settings, Outgoing server tab. Also, confirm with your email provider the proper ports to use - many ISP's block port 25 when connecting to the internet using a different Internet provider.

  21. kim says

    I have Microsoft Outlook and my messages are stuck in the outbox and i am not receiving any new mail.

    The error message reads: The message could not be sent.

    details:
    The message could not be sent because it is being edited.

    error code: -50

    • Diane Poremsky says

      I don't think i have seen that error before.
      What version are you using? Is it the Mac version?
      What type of email account do you have?

  22. amy says

    I've had problems with my Outlook 2007 not sending emails. I have tried multiple websites that all gave the same suggestions for fixes. Your website gave some additional fixes and my problem is now solved!!! THANK YOU!!!

  23. Ray says

    If I open my Outlook 2007 Outbox, all message to be sent are marked as read and are not italic. They need to be unread and with italic headers to send. Opening then and clicking Send made no change.

    I found that iCloud that I'd installed a few days ago was installed in Outlook (Tools>Trust center>Add-ins) and requires Adminstrator to disable. Suspecting iCloud I used Windows Control Panel > Programs and Features to uninstall iCloud and now Outlook send works properly.

  24. sean says

    Ray you saved my life!!!! I was pulling my hair for 2 days not understanding why emails are being held in my outbox for no reason. I would have never found it in iCloud.
    Thanks a TON!!! That did it

  25. Eloise says

    This typically happens when traveling, because most public places block the Port 25! Ypu can try to set it to 2050, or use a SMTP service
    Hope this helps,
    Eloise

  26. Sandy says

    Ray - I had the same issue. And removing icloud helped as you said. So do you suspect icloud and Outlook do not run well together?

  27. Martin Purdy says

    I too had the same issue: items not sending and lesft in the outbox. Somehow the emails in the outbox had no date on them (I was replying to mac emails). I created the emails from fresh, which set the date correctly, and they then went through.

  28. Red Dave says

    Thanks. my outgoing port was set to number 25. I changed it 587 as suggested and it worked. No idea why it defaulted to 25.

  29. joseph edmondson says

    I have been having a problem with my Outlook 2007 ever since the outlook connector got added. My email has been hanging...reading receiving message 1 of 1 on the status bar. Once I close it, it will not reopen without a reboot. I have followed your advice for removing my avg antivirus in the com settings, but it says I am not an administrator and will not remove it. Any advice? I have done all the updates and I'm getting to the point where I just don't want to use outlook anymore. Thanks.

    • Diane Poremsky says

      Close Outlook then hold Ctrl+Shift as you right click on the Outlook shortcut. Choose Run as Administrator. See if you can disable AVG add-in. You may also be able to disable it in the AVG options.

  30. Steve says

    Hey folks. Have mail in the outbox that you can't delete? Here's the simple solution that works for me every time. Shut down your computer. Unhook from the internet. Re-start your computer. Open Outlook, go to outgoing mail and delete the email. It's now gone. Hook the internet back up and presto...

  31. Jim Clark says

    For those of you who find that your email gets stuck in your Outbox when the iCoud add-in is active, try this.
    1. Go to your Outbox and double-click to open the email that won’t send.
    2. Now highlight any folder other than the Outbox.
    3. Go back to the email that won’t send and add a keystroke (I usually go to the end of my reply and hit enter).
    4. Now send. Make sure you do not go back to the Outbox while sending
    I don’t know why this works for me (and it may not work for you), but it does, and is easier for me than de-activating the iCloud add-in every time I want to send an email.
    I am on PC Windows7 64 bit, 32 bit version of MS Office 2010

    • Diane Poremsky says

      No need to deactivate the icloud - the messages should send if you open them, switch folders then hit send.

  32. Greg says

    I'm having an issue with Outlook saving my sent emails in the incorrect folder.
    For example:
    If I send an email from my yahoo account in outlook it saves the sent email in "Personal Folders-Sent Items." It doesn't save it in my Yahoo's Sent Items folder.Now when I sign into my Yahoo account on the internet the email I sent does not appear in my Sent folder. I did find one solution. I can drag the email out of the Sent Items folder (in Outlook) and drop them into my Yahoo's Sent items folder (in Outlook). It then syncs with the internet and I'm able to see the email on Yahoo's mail server. Also when I send mail from my Yahoo account using their mail server the email shows up in my Outlook's Yahoo-Sent Items folder. I just want it to be able to work the other way around. Is there a way to bypass the solution I found or do I need to drag and drop the email every time?

    • Diane Poremsky says

      What version of Outlook? You can set 2007 and 2010 to use the IMAP accounts sent folder - file, Account Settings, double click on account then more Settings dialog. In all versions, you can use Rules to move the mail to the imap folder.

  33. Greg says

    I'm using Outlook 2007.
    It worked though! Thanks!

    One more question.

    I setup my Gmail account on outlook but the account doesn't show up on the left hand side with the rest of my email accounts.

    When I go to Tools-Account Settings it shows up with the other email accounts so it is setup properly.

    • Diane Poremsky says

      It's set up as an IMAP account or POP3? If POP3 and delivering mail to the default datafile, it won't be listed separately in the navigation pane.

  34. Chris says

    Hi Dianne,
    I have my Gmail account attached through Outlook 7 (Windows 7) and have a similar, if not exactly the same problem to some others who have posted here. Some - not all - emails won't send. More than often, it is replies that are the main offenders. These are not large. Some are one liners, and when I look in the Outbox, I see that the font of the messages that refuse to send is in regular script. (Those that send successfully appear in italic script.)

    I've found that if I copy the body of the message, leave the original (non-italic) message in the Outbox (this appears to be important), then go back to the Inbox, reply again from the original message, paste the message I've already written, check that the second copy is displaying in italic (it doesn't always) then it will go.

    My wife is frequently at screaming point over this, as she won't go through this convoluted procedure, and I can't say I blame her. I use Zone Alarm Professional as my firewall/antivirus suite. Can you suggest a fix?

    • Diane Poremsky says

      Do they send if you don't look in the outbox?
      Do they send if you use Safe mode? To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

  35. Chris says

    Hi Diane,
    Looking or not looking in the Outbox doesn't make any difference. (But to repeat myself, just to confuse the issue, some do send, some don't. I can't see what's different about those that successfully send on the first attempt.)

    I opened Outlook in Safe Mode as you suggested, and a message I created in Safe Mode sent successfully, leaving one that I'd created earlier in the Outbox.

    Chris

    • Diane Poremsky says

      What antivirus do you use? When Safe mode works (and assuming it works long term) the problem is either a support file or addin. I'd find and delete the *.SRS file (holds send and receive settings) and disable all addins.

      Paste %appdata%\microsoft\outlook in the address bar of windows explorer and press enter to open the folder where the SRS file is.

  36. Fred says

    I am using Outlook 2002 SP3 in Win 7 and have had the problem of stuck messages for months and have tried everything that Google returned. Finally, I found that I had four Contact files, two were not valid and the default wasn't the right one. I deleted the invalid ones and reset the default, and Presto!, Outlook is working now. I haven't seen this solution anywhere and others may want to try it.

  37. Jerry Jackson says

    This doesn't help at all. All my settings are fine. I send emails fine all day. The size isn't an issue. Randomly one in a few dozen emails gets stuck no matter how small or brief it is, and other emails in the outbox are sent.

    • Diane Poremsky says

      Any error messages? Its possible the address is bad or the server is not talking with outlook and outlook can't send the message, especially since it's very random.

  38. dustin says

    Our Microsoft Outlook 2007 has all of a sudden stopped working. It is extreamly slow opening the program and it will not send emails. We have tried repairing with the disk and that did not help. Is there anything else we can do to fix this. It has had us shut down since last week.

    • Diane Poremsky says

      Do you get any Send and Receive error messages? Did you test it in Safe mode?

      To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

  39. Andrew Eisner (@aeisner) says

    I have a mysterious problem that just cropped up with one of my email accounts. Yesterday two of my email accounts (my personal one and a work acct) weren’t sending emails through outlook – another acct was sending fine. Nothing had changed other than trying to set up email accounts on a new laptop. I was finally able to get my personal acct to send by changing the outgoing port to 465 but nothing seems to be working for my work acct. Another worker says it works okay for him but I can’t get it to work on any of my computers including my iPhone. Any ideas? I’m on Comcast by the way. Could Comcast be blocking it? Why would it stop working all of a sudden - I can't even get it past the test message in outlook setup

    • Diane Poremsky says

      Try port 587 too. That is commonly used. Did your antivirus/security software get updated? If the software integrates with Outlook to scan email, an bad update may cause problems.

  40. Andrew Eisner (@aeisner) says

    Here's an update my previous question. I went to starbucks and I could send out of outlook just fine. Any thoughts?

    • Diane Poremsky says

      It sounds like your ISP is blocking, but it could be a firewall or router at fault too. Is the account that works a Comcast account? If so, they are blocking ports.

  41. Andrew Eisner (@aeisner) says

    No it's not a Comcast account. Here's more evidence it's Comcast. On my iPhone I can send on WiFi outside my house, 3G inside my house, but not on WiFi inside my house through Comcast. The problem is after 11/2 hours on the phone with Comcast they said it wasn't their fault and there was nothing more they can do. How do I get Comcast's attention. I'm actually a tech journalists, should I go that route? What do you think?

  42. Andrew Eisner (@aeisner) says

    One more update, turns out Comcast is rolling everyone over from port 25 to port 465 SSL with authentication. I just have to see what my email server needs for that.

    • Diane Poremsky says

      First we need to figure out why its not working. What have you tried so far? Do you get any error messages? What exactly happens?

  43. Dave Meredith says

    Diane,

    I have Outlook 2010 trying to setup a Gmail account and it won't send the message out of the outbox. I've tried several ports, but nothing goes. However, when I use port 25 the test message goes through but when I finish and send my own messages it still hangs in the outbox...windows 7

    • Diane Poremsky says

      Gmail uses these settings:
      Outgoing mail server (SMTP): smtp.gmail.com
      Use Port 587, Use TLS (More Settings, Advanced tab)
      Require Authentication (More Settings, Outgoing Server tab)

  44. Anna says

    Hi Diane, Outlook 2010 problem with sending the message, it is only showing "Sending message 1 of 1" and it is stuck in the Outbox and then "Send/Receive error" shows at the bottom and nothing happens... I am not sure what should I do while testing in the Safe mode? Internet connection seems to be fine, all the settings too. Don't know what to do..

    • Diane Poremsky says

      Do you see the message in the outbox? Is it bold and ready to send? If so, restart in safe mode and see if it sends. If it's not bold, open it then switch to the inbox before clicking the send button.

  45. Dave Meredith says

    I have these settings and the test email goes but when I send one myself from the account it stays in the outbox...

    • Diane Poremsky says

      Gmail should work with those settings. What antivirus do you use? Can you send mail if you use Safe mode?

  46. Anna says

    Hi Diane, Yes it is in bold in the outbox folder, also it doesn't send when I try in the safe mode. When I opened in the safe mode was also in bold. I have it now in the inbox. I have no idea what is going on... Together with my husbund we have the same problem as his outlook has additional account which I am using. He has the same problem on his PC, I have problem on my laptop. What is strange he can send emails from the same outlook box from the Ipad or his phone... any ideas?

    • Diane Poremsky says

      What type of email account? Do you get any send and receive error messages? Open the Send and receive progress dialog to check.
      Are you authenticating with the outgoing server?

  47. regina417 says

    Many thanks for this post, I followed your directions and my stuck messages got sent. Technology is great when it works!

  48. Mike Loomis says

    Hi Diane - You have some great info here - thanks! I've looked around and tried some things and am still having problem sending emails with my Outlook 2010. I'm suspicious of a couple things that I did prior to being out of town. I backed up outlook. and I sync-ed my iPad, and updated the iPad operating system. When I returned, I could receive emails but not send. I've checked and re-checked all my SMTP settings, but I use 4 different POP3 addresses and all four are doing the same thing. Any ideas, please?

    • Diane Poremsky says

      Who is your email provider? All 4 using the same server? Verify they did not change the SMTP server setting.

  49. Mike Loomis says

    Hi Diane - I backed up my Outlook before heading out of town, and also sync-ed my ipad. I don't use Outlook when I travel because I usually don't know SMTP settings, of course. When I returned home, I could receive emails but not send - same issue with all 4 of the POP3 email accounts I use. I've triple checked settings, and chatted with Comcast, tried changing my port settings, etc - I just get an array of different error messages. Any ideas? Wondering if something glitched when I backed up or sync-ed? Thanks!

    • Diane Poremsky says

      Oh, Comcast. I'm pretty sure it's the change in their configuration. I don't think its the sync or backup.

      What are the error messages? They may give me a clue.

  50. Mike Loomis says

    Thanks for the fast response!

    When my settings are as they were (No SMTP authentication, Port settings at 110 and 25, no SSL) after about 10 seconds, I get this error:
    “ Task 'Mike@domain.com (WP) - Sending' reported error (0x80042109) : 'Outlook cannot connect to your outgoing (SMTP) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).'”

    and...

  51. Mike Loomis says

    When I change SMTP port to 465 and no SSL, I get this error message after 30 seconds: (and it keeps re-trying)
    “ Task 'Mike@domain.com (WP) - Sending' reported error (0x800CCC0F) : 'The connection to the server was interrupted. If this problem continues, contact your server administrator or Internet service provider (ISP).' “

  52. Mike Loomis says

    And... When I change above SMTP to “SSL” I immediately get this:
    “ Task 'Mike@domain.com (WP) - Sending' reported error (0x800CCC78) : 'Cannot send the message. Verify the e-mail address in your account properties. The server responded: 550 5.1.0 Authentication required' “

    I’ve also tried “Require authentication” and it repeatedly prompts for the UN and password…

    (sorry for these three replies - when I posted the whole reply I could not submit the comment)

    • Diane Poremsky says

      Yes, the submit button sometimes disappears - tabbing should bring up the fields so you can submit.

      On the Outgoing server tab, are you authenticating with the server?

  53. Mike Loomis says

    One more bit of info - while traveling, I probably opened Outlook accidentally once or twice, and quickly closed it down. Wondering if that got some startup thingy stuck. Again - thanks!

  54. Mike Loomis says

    "On the Outgoing server tab, are you authenticating with the server?"

    No - I tried it, but very willing to try again! What settings do you advise? Thanks!

    • Diane Poremsky says

      Usually you would use the option to use the same settings as incoming email. Don't use SPA unless your server supports it (most don't.)

    • Diane Poremsky says

      If you checked and triple checked everything in Outlook, check your firewall then your router. Is either blocking ports?

  55. Mike Loomis says

    I did do a windows update the day before I left - Could there have been some Windows/Outlook security update that changed something? On my router - I haven't made any changes there - ?

    • Diane Poremsky says

      Check Add/Remove programs for the update history. At this point anything is possible, although i think its highly unlikely.

  56. Mike Loomis says

    There was a Windows update, which included an Outlook update, I did the night before. But I was able to send emails the following morning. How would I see if any ports were being blocked by firewall or Router? Again, than you, Diane, for your time!

  57. Mike Loomis says

    just the firewall built into Windows 7, I suppose. I just checked and it was enabled. So I turned it off, and still had no success sending.

    • Diane Poremsky says

      The windows firewall usually won't have problems after an update. 3rd party firewalls can. Are you still getting the same error messages?

  58. Mike Loomis says

    Yes - I've tried all the combinations of port settings, etc... Or at least all but the one that works! ;-)
    My old default settings of 110 and 25 ports, no SSL, etc. get this error:

    Task 'Mike@____.com - Sending' reported error (0x80042109) : 'Outlook cannot connect to your outgoing (SMTP) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).'

  59. Mike Loomis says

    I have 4 different POP3 addresses, and none are "@comcast" - that's what's so weird - all 4 receive fine, but wont send. Each is from a different email server. ??

    • Diane Poremsky says

      It sounds like Comcast could be blocking. Is the email account the one in the earlier posts? According to network-tools.com, it is using hostgator for mail. If so, try port 26. According to hostgator support, they use port 26 as an alternate.

  60. Mike Loomis says

    Thanks, Diane! I will try some more things, including checking your suggestions above, in the morning. Really appreciate your time!

  61. Mary Guenther says

    Mike and Diane,
    I have been following your conversation the past few days. I, too, have issues sending emails on my business account....and I've never had any issues until this week. I also use Outlook 2010. I have received the same messages as Mike and I have tried all the suggestions you have made...none have worked. My original port settings were always:
    Incoming: 110, Outgoing 587. I have contacted the group who hosts my mail server today, but have not yet heard from them. My personal POP account is with Comcast. Did something possibly change with Comcast POP accounts that affects IMAP accounts?

    • Diane Poremsky says

      Are you having problems with a Comcast account or a non-Comcast account? If non-Comcast, who is your email host? I was told Comcast just started blocking ports, so any account that uses port 25 won't work.

  62. Mike Loomis says

    Hi Diane - Spoke to comcast (for the THIRD time) and they finally told me they started blocking port 25, but the new item was that if my POP3 providers didn't support port 465 or 587, that I COULD use Comcast as my outgoing server. Yeesh. Thank YOU for all your help!

  63. Mike Loomis says

    Comcast told me that they have been rolling out the port changes, and it probably hit me last week. (They also said they sent an email out about it, but none came to me). Basically I used my Comcast email address as the outgoing server - you do this by checking "my SMTP requires authorization" and selecting your comcast email (***@comcast.net) and your comcast account password. Then you use port 465 and select SSL. The "good" news is that I can now use outlook when I travel.

    • Diane Poremsky says

      I'm not sure I understand the question. Do you have an application that sends mail to Outlook, but those messages are stuck in the Outbox? Outlook needs to be open to send mail.

  64. Ash says

    3/29 was the last time that I had a "sent" item. I too am running 2010 and cannot send email. THey are stuck in my outbox. I use comcast as well. Sounds like these are linked but I am a novice about connections and need help finding out how to re-route or fix my problems so I can send email. I can send from my iphone.
    thx

  65. Ash says

    Hi,
    This is the error I receive after changing to port 465 and selected SSL:

    Send test e-mail message: Cannot send the message. Verify the e-mail address in your account properties. The server responded: 550 5.1.0 Authentication required

    • Diane Poremsky says

      On the Outgoing server tab, did you select the option to use the same settings as the outgoing server?

  66. Doug T says

    Hi Diane,It looks like you've covered this 100 times but I don't really understand what to do. We receive messages fine, no problem. But neither new messges or replys go out. They just sit in "the out box" and nothing happens. No errors, not waiting to send, nothing. So where do I even start? Thanks in advance!

    • Diane Poremsky says

      Do they send if you don't look in the outbox? If so, an addin (icloud & onenote will do this) is the problem. Either get rid of the addin or stop looking in the outbox.

      Does it work in Safe mode? If so, the problem is an addin. (To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.)

  67. SHickey says

    Thank you! I have been looking everywhere help sending messages out of Outlook and it was the Comcast outgoing server port change to 587 that did the trick!

  68. Steve Campsall says

    Hi
    What I find with the new Outlook 2013 / 365 is that if I dare to look at any post in the Outbox, to see if it's going to the right addressee for example, then that's it - it won't send. The italicised non-bolded email loses its italicisation and become bold, and is stuck, requiring it to be sent all over again. It's definitely a problem with the coding of the program - nothing to do with file size or anything.

  69. simon Salvin says

    Hi Diane,

    I have a client who uses Outlook 2013 with a Hotmail account, I have created a new data file and imported her contact groups in to it, however when sending an email to a group she receives an unknown error message. I asked her to minimise the amount of contacts in a group which she has, but any more than around 20 contacts in the group and she receives the error? Any ideas? Many thanks.

    • Diane Poremsky says

      The contact groups are probably broken. Open one, choose Forward > vcard in internet format (This creates a text file as a backup).
      Click the update button.
      If any are removed, you can copy the email address from the text file created when you hit Forward.

  70. Grant Lester says

    Hi Diane,

    I am using outlook 2003 and windows 7. My outlook wont send emails, but will receive them. I created a new account with identical settings on my laptop and that worked, so I guess its not the isp. I deleted iCloud, deleted AVG and repaired outlook, to no avail. I booted outlook in safe mode and created a fresh email, but it wont send either. I changed the folder I was viewing, still nothing. I am using port 587 for outgoing mail as instructed by BT, my isp. Send and receive completes with no errors. I ran "test account" it passed and sent a test email that I did receive after a new send/receive. I dont know what to try next! Can you help me?

    • Diane Poremsky says

      There are no errors in the send and receive progress dialog? Are you authenticating with the outgoing server? Is this a BT Yahoo account?

  71. martinip says

    hI dIANE, Do you have any suggestions- I have installed a new HDD on my windows xp pc and reloaded all software. I have the same software config as my laptop for Outlook (where gmail send works), I have the same config for the anti-virus/ firewall app (kaspersky) and I have tried safemode (where I still can't send email) but yet i still get the error that the test email can't be sent and I need to check my email address. (all server comms in pop and smtp are fine with google and I don't have another email address to test if it just a google issue on this pc).The ports are fine with the ISP (bethere) 995 and 465 so I am at a loss now for what to do. Thanks! Martine

  72. martinip says

    Hi Diane, Just fixed the problem. It was a sp3 office xp uo-date I needed.
    Best wishes, Martine

  73. Herb says

    Grant, I had the same problem and it turned out that iCloud was indeed the culprit. I uninstalled it, rebooted, and am back in business. You said you uninstalled iCloud; double check that no components were left behind. Did you use the Windows 7 uninstall facility and did you get a confirmation from iCloud that the uninstall was successful?

  74. mint says

    Got a problem with OL2007. For some reason OL2007 has now decided to receive incoming emails into the outbox.

    • Diane Poremsky says

      As long as its really new mail and not mail you sent that outlook isn't moving from the outbox... Check rules and then run scanpst.

  75. ken knight says

    About two weeks ago, outlook quit sending "reply to" messages. They are just stacking up in the outbox. There is no problem with emails that I originate. They are not large files (the biggest being 176 kb. Any suggestions?

    • Diane Poremsky says

      Any send and receive errors? Are all replies affected or just some? This usually means there is a problem with the reply to address or account.

      What type of email account do you have? If POP3, Close Outlook and run scanpst on the pst.

  76. Martien de Jong says

    Is a full mailbox a possible reason? I had a mail that got stuck in my outbox but other mail were sending fine. no attachment or anything. When I retyped the mail it got sent immediately.

    • Diane Poremsky says

      A full mailbox should prevent all messages from sending, not just the current one. Unless it had a huge attachment - but even so, there should be a warning (usually via email) that you've reached your quota.

      If retyping in a new message worked, the address may have been corrupt - outlook has been know to add smtp= to addresses, which makes them invalid.

  77. michael Hayford says

    Diane, i am receiving but not sending emails from outlook 365 on my PC, I can send through the online mail option of 365. i was able to send about a week ago and it just stopped sending. i have read a bunch of posts about disabling the icloud add-in and it did not change it. i tried online email (office 365) and it worked. icloud sends apple devices as well as MS office website.

    help!

    Michael

    • Diane Poremsky says

      When the mail doesn't send, what happens - is it marked as read if you look in the Outbox or just sticks there, even if you don't look in the outbox? Do you get any send and receive error messages?

  78. Sheri says

    Hi Diane,
    I am not having a problem but the Pastor here at our church is having problems with his Outlook. We have Outlook 2010 but even his emails coming to me (in the next room) aren't coming through...just staying in his Outbox. Any suggestions? He said he has cleaned up most of his folders now. Thanks!

    • Diane Poremsky says

      The usual cause is an addin. Try safe mode and see if it sends- To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

  79. Joe Scarry says

    I am having trouble sending email from Outlook 201 using my iCloud account> it worked fine until a few weeks ago. I can receive messages and send form Gmail and Verizon accounts fine. I received a message saying there was an unknown certificate and I asked to install. There is a Verisign Class 3 Code Singing 2009-2 CA which expires on 5/20/2109 and another just listed as CA with has expired (it won't let me remove this one).

    I worked with Apple support to verify outgoing mail settings (smtp.me.com, port 587 TLS as SSL did not work) and even tried prefixing p06- as suggested. I also disabled firewall and scanning all to no avail.

    Any suggestions

    • Diane Poremsky says

      Did you install the new iCloud addin? That is causing issues for many people.

      What does the error in the send and receive dialog say?

      In More Settings buttons:
      Outgoing Server tab, select:
      My outgoing server (SMTP) requires authentication
      Use same settings as my incoming mail server
      On the Advanced tab, Outgoing server (SMTP) Use port 587 and enable TLS.

  80. Benjamin says

    THANK YOU Diane, although it wasn't an antivirus persay...what you said about email scanning software led me to the windows firewall, when I disabled that my E-mails immediately sent/received successfully! thank you

    • Diane Poremsky says

      Check the firewall settings and make sure Outlook.exe is allowed through- that is the usual cause when firewall blocking access to email server.

  81. John says

    Diane, I am having similar problems as other people commenting here and so far following some of the suggestions here still have not been able to automatically send emails. Specifics: Outlook 2010, Norton NIS, Provider Comcast, Outgoing Server SMTP port 587, TLS enabled. I had ICloud 3 but based on other comments removed it using add/remove program. I receive email fine but when I send the email goes and sits in the outbox, if I open the email in the outbox and hit send it sends fine. There are no error messages and the same thing happens if I run Outlook in Safe Mode. This is happening on a Laptop running Win 8 and a Desktop running Win 7. Appreciate the help.

    • Diane Poremsky says

      Norton is suspect - it is well known to cause problems like this. Because of the way Norton (and others) are designed, they are deeper into the system and safe mode won't always bypass them. Disable the Norton and iCloud addin and see if it works.

  82. Heather says

    Hi Diane,
    I am having a problem with Outlook 2013. It sends and receives fine, but when I create a new e-mail it sits in the Outbox. If it is a reply, it gets sent away immediately. If I go into the Outbox, double click on the e-mail and send again, it will get sent immediately. I just can't seem to get them to send without having to go into the Outbox.
    Any help would be great!

    • Diane Poremsky says

      What type of email account do you use? Are you addressing it from the address book or typing part of the name and selecting it from the autocomplete list?

  83. Heather says

    Thank you for your reply, I actually figured it out yesterday though. It was the Norton add-in that was causing the problem. I disabled the add-in and now it works perfectly. Thank you!

  84. Gayli Craver says

    Diane,I am not able to send meeting invitations (or responses to meeting invitations) in Outlook 2010. My ISP is Comcast. I have also tried disabling Norton to see if that was the problem, and it didn't make any difference. I have also tried starting Outlook with no add-ins and that did not help.

  85. Gary L. Stokes says

    Diane -- I am having problem of not being able to send Outlook E-mails. I am staying at RV Resort and using their wireless service. I can receive but not send. I have had my Dell Lap top checked out and it is AOK -- all settings have been checked and everything appears to be right. I can send E-mail using internet web site from my provider. Any suggestions.

    • Diane Poremsky says

      Did you check the outgoing authentication ? This is under More Settings in your account settings. What port # are you using? Do you get any error messages?

  86. Nicholas Koriakin says

    Hello Diane,

    My Outlook 2010 emails get stuck in Outbox. I can send them if I double click on each in the Outbox, then Send. I realized this after a number of days, I did not get a response from those I 'sent' the emails.

    Your help will be much appreciated.

    Thank you,

    Nick Koriakin

    • Diane Poremsky says

      They'll send you open them and resend, but if you copy and paste the address they send ok the first time? I'll see what I can find out-I'm meeting with the product team this week and will add it to my list.

  87. Robert Mapes says

    Hello Diane, I am having the same issues as Nick. This just started in the last 10 days. Outgoing stuck in Outbox. If I open them then hit send they go. Auto send feature seems to be disabled??

    Thanks
    Bob Mapes

    • Diane Poremsky says

      he update server should send them down automatically but may not install it for a few days if you don't reboot. Are automatic updates enabled in file, office account, office updates?

  88. Neil says

    Hi Diane please can you help. I have a colleague who runs a small business. He has a server (sbs 2003), 3 windows pc's and a mac all running either outlook 2007 and 2010 (pop). One windows pc sends/receives one outlook mailbox and the other two send/receive the other mailbox. The server has IA mail server installed - from an old company called true north software who ceased trading. When he sends an email from his mac to the two pc's using the same mailbox they get stuck in this IA mail server and never get delivered. When he sends to the other pc with a different mailbox or to external email addresses they get delivered. All the windows pc's are sending and receiving emails ok including to the mac. Thanks in advance for your help.

    • Diane Poremsky says

      So the mail leaves the mac outlook outbox but doesn't get delivered? Are both new messages and replies stuck or lost, or are only new messages lost? Does he get any sort of bounce message back? Without any type of error message, it will be hard to troubleshoot.

  89. Tyler says

    Hi, Diane -

    My outgoing e-mails seem to only get stuck in my outbox when sending from home, but never when I am sending e-mails from work. What causes my e-mails to send successfully when I am connected to the internet from one location via another?

    Thanks!

    Ty D

    • Diane Poremsky says

      Do you receive any send and receive error messages?
      Check your authentication - In 2010/2013, go to File, Account Settings, double click on the email account the Outgoing tab. Are you authenticating with the server? Common is to use the incoming account/password. Also check the advanced tab - if your smtp server accounts a different port #, try it.
      How to send email when traveling

  90. Tyler says

    Thanks for the quick response, Diane.

    No error messages, and I've already checked the "My outgoing server requires authentication" box. In truth, I don't know about the ports and am not sure how I would find out? And does this mean I have to manually change this every time I'm sending e-mails from home vs. work?

    Thanks,

    Tyler

  91. Robert Mapes says

    Diane, I was having a similar problem and traced my stuck outgoing email to Norton security checking. I disabled Norton from checking my Outlook email and it solved my problem. Merry Christmas

  92. John Cosgrove says

    Diane, thanks for being so helpful. Wanted you to know that I was having a somewhat-different problem with Outlook 2007: my outgoing emails got sent, but they never left the outbox. Since they didn't show up in the sent folder I was never sure if they actually had gone. After reading this thread I tried running in safe mode and removing the Norton antivirus add-in. Neither of those helped, but then I ran scanpst.exe and that fixed the problem. Thanks!

  93. EnoughWithMS says

    For a while there I was irritated with MS outlook or whatever the MS mail is called for sending some days and not sending other days and then maybe sending for some hours and then not. Notable when traveling overseas. OK, no problem. Went to gmail and have not had a no send problem, or any problem with email. WTF MS

  94. Jo says

    I have tried to send an email through outlook by opening the email, switching folders and hitting send. Did not work. Have disabled iCloud as most people are finding this is the issue. Did not work. Any other suggestions? The email is 4MB's. Is that too big?

    • Diane Poremsky says

      4MB could be too big, it really depends on your mail host, some don't allow larger messages. do you get any send and receive error messages? Did you try Safe mode? To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

  95. Jo says

    At first there were no error messages then after I disabled iCloud an error message occured. I will try in Safe Mode and let you know how i did. Thanks

  96. Dan says

    Random emails won't leave Outbox in Outlook 2007. It seems that once one email is stuck, the others in the cue will not send either. If I reboot the computer and open OL the messages will send.

    One MAPI email account
    Uninstalled iCloud
    Disabled all Add-Ins.
    Disabled SMTP email scanning in Avast.
    Checked for read receipts with MFCMAPI, there were none.
    Scanned with scanpst and compacted unicode pst.

    Out of ideas, would creating a new profile be a possible solution?

    • Diane Poremsky says

      Do they stick if you use Safe mode? Are they getting marked as read or just not sending?

  97. Dan says

    Diane, thanks for the help with this. Yes, the messages do get stuck in the outbox while in safe mode. The messages are not marked as "read."

    • Diane Poremsky says

      If it happens in Safe mode, then its unlikely an add-in. It's something internal or more likely, external. You can try a new profile. I'm not sure if it will fix it or not, but I'm out of ideas.

    • Dan says

      Although it was a while ago, I found the problem in my case was Avast Free Antivirus. I tried turning off the email scanning and other things with the program, but only removing it helped. I then switched to AVG Free and the problem didn't return. The current version of Avast may not be a problem, but since I switched I have not gone back to it.

  98. Brad says

    Randomly came across this site - hope you can help!
    - three of us just updated to office 365 for email and use office / outlook for mac 2011, locally. I am only one of (3) that can now only receive emails in my outlook for mac 2011 - but cant SEND any emails. I hve my Office 365 web mail page open - and that works just fine. I cants see here to change any settings on the local machine side of this macbook pro and outlook - as the set up was an automatic process and says I am connected to the exchange server just fine. I have deleted the exchnage profile and reloaded it multple times now.

  99. Brad says

    I shoud lhave added that THIS is the specific Error I am getting:
    "The user account which was used to submit this request does not have the right to send mail on behalf of the specified sending account."
    Error Code: -19721

    • Diane Poremsky says

      is this a shared mailbox? it looks like you don't have send as permission for the address.

  100. Mark Williams says

    I had this exact same problem and for the life of me couldn't figure out what was causing it. I called Office 365 support and they didn't have a solution either. I even did a hard reset on the router and no difference. Out of desperation, I swapped out their D-Link Router with a Linksys router and the problem disappeared. There may have been a setting on the D-Link router I could have changed, but I figured a hard reset should let email pass through, so I just swapped out the router. I thought I would post this in case others were having the same issue.

    Hope it helps,
    Mark

    • Diane Poremsky says

      Thanks for posting. My best guess is the router had a firewall that was enabled and blocking the port.

  101. Peter Storti says

    Hi, I am not able to do several things:
    1- send new e-mail from my Pop3 account
    2- Save contacts when offline

    Outlook2010 - I have an exchange mail account with ost file but the default mail is a POP3 account. The default is set to the POP3 account. I have started Outlook in safe mode and the problems persist.

    When trying to send from the POP3 account I get this message:
    Task 'peter.storti@infoedge.org - Sending' reported error (0x80040115) : 'The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.'

    I get a similar message when trying to save a contact.

    This is not logical since I'm using the POP server to send not the Exchange server and I should be able to save locally when offline. When I am connected to the Exchange server POP server is not able to connect because of the VPN settings.

    I can reply to e-mail via the POP3 account.

    The saving contact problem is sporadic where sometimes it works and sometimes it doesn't.

    If I have received an e-mail from someone I was able to create a new e-mail and send in safe mode and send via the POP account but could not do the same thing with a new e-mail address.

    I tried the Work Offline setting and Outlook doesn't even try to send through the pop account. After unselecting the Offline option it still does not try to send. Outlook is not trying to send or receive from the Exchange server after using the Offline option...I have restarted Outlook and that is still the case.

    • Diane Poremsky says

      You're using VPN to the exchange account? Is the pop's pst set as the default data file?
      You should keep the accounts in separate profiles. Exchange likes to be in charge and save all appointments and contacts to it's mailbox.

  102. Mari says

    When we generate an email, we are able to 'delay send' it without a problem. However, we have payroll software that also automatically generates email (pay vouchers/reports) that, although we manually select 'delay send' in Outlook, will not delay sending.

    Our IT peopley are stumped. They spoke with the payroll software developers and they say it's an Outlook issue, but our IT people cannot find any problems with Outlook. I notice most add-ins are disabled on our system.

    Any suggestions?

    • Diane Poremsky says

      Are you using a rule to hold for nn minutes or the do not deliver before option?

      I'm guessing the software hooks into Outlook after the point at which outlook sets the delay.

  103. Elaine Dodge says

    Hi Diane, I am using a borrowed computer and have transferred all my data from my old machine onto this one but now my emails won't leave my outbox. Everywhere I go to find help talks about going to tools - there is nothing on my outlook that has this. I really need this sorted as I have to get quotes out. Having done a bit of a search it seems the version of outlook I have dates back to 2006. PLease, please help. Not very computer savvy eiter which doesn't help. Thanks.

    • Diane Poremsky says

      Outlook 2007 and older have a Tools menu, Outlook 2010 and 2013 have options and other settings on the File command.

      Do you have a Help menu? If so, look at Help > About to get the version. Or post a screenshot of Outlook and I will be able to identify it.

  104. Clive805 says

    I've been having the same issue as the one reported here. However, I don't know if this will fix the problem for everyone, but when my mail gets stuck in the MS Outlook without sending, I simply restart my router and then all seems fine again. The mail gets sent and the outbox is cleared.

    Although I live in the U.K. and my router is supplied by British Telecom, it's been reported elsewhere that this particular router, and also certain other routers, do have a tendency to get "stuck" during MS Outlook communication, and may also cause the WiFi connection to be dropped, or to freeze.

    At least, by trying a router restart first, this will quickly verify if this will work for you too. I hope so.

  105. Claire says

    Diane, I have the same problem as the very first question in this thread..but there seems to have been no reply.

    When hitting reply to email it gets stuck in the outbox...one line emails. I have to retype the address in to get it to go.

    I think it can't read the autoformatting of Outlook email address.

    Help! I am on a Dell, windows 8 and outlook 2007.

    • Claire says

      All replies and when typing a new email I have to tyoe in the whole email address and can't use the autofill as it enters different characters at start and finish of email address. Ie won't send.

      Just suddenly stopped working.

      just use windows security.

    • Diane Poremsky says

      clear the Autocomplete list and see if that fixes it. In Outlook 2010 or 2013, this is in File, Options, Mail - about 2/3 down the page.

  106. Claire says

    Finally have solved it. It was similar to another answer in advanced settings outgoing server I had to change to SSL to work. Thanks for your help. This was sky email

  107. Reg Admin says

    Another issue for laptop users is that Outlook gets confused when both Wi-Fi and Ethernet are connected. We have a Dell Latitude, Win7Prox64SP1, Outlook2010 Pro Premium (all current patches and updates) user whose Wi-Fi doesn't auto-disable when the asset is docked and connected to Ethernet. Email sent gets stuck in outbox until a reboot. Lenovo laptops have a connection manager that ensures the radio is disabled when Ethernet is present.

    Is there anyway to either force Outlook to seek the strongest connection or to make Win7 disable Wi-Fi upon hardwire connection?

    • Diane Poremsky says

      No and No. The computer should switch to the best connection but as you've noriced, Outlook doesn't switch over and tried to use the old connection. If you set Outlook offline for a few minutes, does it work again? My recommendation is to set outlook offline or close it before changing the connector.

  108. Brian says

    Dear Diane,

    We are based in Namibia where we run an emergency medical service. The day before yesterday, Outlook on two of our machines (one running 2010 and one running 2013) started acting up.
    On the 2010 outlook the following is happening:
    We can receive e-mail.
    Suddenly messages are being stuck in the outbox - but only those with attachments (not large attachments - (339Kb) or those where we select "reply".
    We use Avast anti virus. Following advice on this page, I have disabled the anti virus. No change.
    I have tried logging the problem - no log appears in the temp folder...
    I have tried using MFCMAPI... it looks different to all the examples I see here or on their page. There, is however, a SPOOLER_FAILURE event - but I wouldn't know how to fix it.
    I have tried removing add ins - but although I am the only profile on this machine.. it tells me I need administrator privileges.. (My profile IS the administrator profile)....
    I haven't yet begun to look at the 2013 Outlook on the other machine.
    The 3rd pc in our office is running 2010 without any problems...
    Please would you be kind enough to provide help and advice (designed for a simple person.. me!). We heavily rely on the pc's and Outlook for everything we do to ensure that the emergency service operates properly, particularly as we are sited in a remote area and cannot just pop into the local shop for help!

    • Diane Poremsky says

      Does it work if you restart outlook in Safe mode? To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

      To get past the admin privilege error, close outlook, hold shift+ctrl and right click on the outlook icon - there should be a command for run as administrator.

  109. Catherine says

    Hello, my dad can't send emails from his phone. When ever he tries to send one if goes into his outbox then says sending failed. There are no attachments, just saying 'Testing'
    This problem has been going on for a while now and we can't seem to fix it.
    If you know what to do that would be great.
    Regards Catherine.

    • Diane Poremsky says

      Is this a gmail account? Does incoming mail work ok? Which phone system is it - iPhone, android, or windows phone?

      The SMTP server name, the port @ and authenticating with the server are the usual culprits.

  110. Debashis Nandy says

    regarding outgoing messages stuck in outbox not going out in outlook 2003: Please go to control panel select programs install/uninstall. click on Microsoft office 2003 and you can see a repair tab coming up. click on repair it will correct the issue and mails will go out. I have solved my issue like that. Thanks Debashis

  111. walter says

    Diane,

    There may be yet another reason for stuck emails. I spent all morning trying to send an email but it wouldn't leave the Outbox. Other sent emails before and after did go.

    8. In Outlook 2013, you have one of the attachments in the message to be sent open. This puts the message in Edit mode (or something like that) and prevents it from leaving the Outbox while the attachment is open.

    Is there a switch somewhere in Outlook 2013 to override the open attachment condition?

    I recall this happening in Outlook 2010, which warned you about open attachments, but let you send the message anyway after you acknowledged this fact.

    • Diane Poremsky says

      That shouldn't affect it in 2013 either. You can't prevent opening attachments in email messages, sorry.

  112. walter says

    I have such a message in the Outbox now, sitting there, while other messages get sent.

    It sits there, with an icon showing a page, with text, and a pencil. I can't find the meaning for this icon anywhere. My best guess is that the icon represents a "Draft" email. Other emails being sent show an icon of an "envelope in motion".

    As a test, I just emailed myself a forwarded email with attachments twice, once with an attachment open and again without opening an attachment. Both emails were sent, so opening an attachment is not the reason why emails get stuck in the Outbox.

    Would you know why "Draft" emails end up in the Outbox? This appears to a stopper for my sent emails.

    • Diane Poremsky says

      That is a draft message. One cause is from looking in the outbox. Try opening Outlook in safe mode and see if the problem occurs (easier to do if it's easy to repro instead of very random.) If so, its an addin causing it.

      To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

  113. walter says

    Thank you very much for your help, Diane. I now have a better understanding of why this is happening and even though I don't have a complete fix, I have a workaround.

    I think you should be designated the patron saint for Outlook miracles. Reading your helpful comments on many Outlook topics and various forums, I see you clearing up many Outlook problems for many frustrated Outlook users. What you've done is given a huge boost to productivity for many Microsoft Office users, and without cost to them.

  114. Joseph Cralle says

    My problem is similar but the evidence seems clear that iCloud Add-In is the problem. Emails when "sent" are placed into the Outbox (until I manually release them via "Send/Receive"). As soon as they have gotten into the Outbox, however, the "Sent" date is missing, denoted as "None." When I remove the iCloud Outlook Add-In (Tools | Trust Center | Add-In) then re-send, the date appears in "Send" column and it releases properly upon "Send/Receive." Half the time when disabling the iCloud Add-In, Outlook hangs and has to be ended (via Windows Task Manager (Ctlr-Alt-Del | Applications | End Task). So, the two don't work well together. But disabling iCloud syncing isn't a viable option either. Whose fault? Surely there must be a solution.

    • Diane Poremsky says

      Yeah, that addin can cause problems too.

      Do the messages send if you don't look in the Outbox?

  115. Joseph Cralle says

    Correct, messages do not send even if I have not clicked into the Outbox. ("Properties" for my folders are set to "Show total number of items" so that I can see the hang up without clicking into Outbox.)

  116. sajid awan says

    hi, i have problem with my outook 2010, when i open my sent items mail it prompt a error message "outlook is stop working and restart itself" please tell me wat i can do...

    • Diane Poremsky says

      It could be one of two things- bad SRS file or bad data file. To delete the SRS file, type or paste %appdata%\microsoft\outlook into the address bar of windows explorer and press enter then delete the SRS file for your profile.

      What type of email account? If you are using POP3, run scanpst on the data file; for other account types, you can delete the data file and let outlook rebuild it.

    • Diane Poremsky says

      No, not the data file. :) Well, maybe if its an imap account, because that is just a copy of the mailbox.

      Delete the SRS file - it holds send and receive settings and is safe to delete. To delete the SRS file, type or paste %appdata%\microsoft\outlook into the address bar of windows explorer and press enter then delete the SRS file for your profile.

      Run scanpst on the data file, if you haven't already.

    • Diane Poremsky says

      Do messages send ok in safe mode?

      To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

  117. Joseph Cralle says

    Yes, the Safe Mode technique works; the offending add-In (in my case iCloud Outlook Add-In) is not loaded. But you can't run in Safe Mode forever.

    So, I have made the iCloud Add-In Inactive, later making it Active again. Email then dispatches fine...until 10-15 emails outbound later they get stuck again in Outbox.

    Why would an Add-In work at first and then cause a problem later? (I even consulted with Apple; very sympathetic and helpful until the problem reoccurred. I called back to the specific rep who had helped; predictably they don't actually pick up incoming calls so I left a voice message with my case number. Now ten days later they haven't called back.)

    • Diane Poremsky says

      If you start outlook with the addin disabled then enable it, it sounds like whatever is causing the stuck messages is triggered after a period of time. I will try to repro this scenario.

    • Diane Poremsky says

      BTW, are you using an apple address (iCloud.com or me.com) for email? I can't repro problems with iCloud in my profile, but I'm not using my apple address for email and removed it from my profile.

    • Diane PoremskyDiane Poremsky says

      ?Is it still acting up? I still can't repro problems here, but I also know that the icloud causes problems with stuck mail for others.

  118. Jean says

    In my MS Outlook 2007, I have multiple (several hundred) messages in the Outbox and they are marked in bold, but NOT marked in italics. Hence, I cannot send them unless I open each message individually and hit the Send button :(

    Is there an option to send all these messages at once, and not ony by one?

    • Diane PoremskyDiane Poremsky says

      Do you have any idea why they aren't sending? Is the envelope icon opened or closed? If it's a closed icon, try restarting outlook in Safe mode and see if they will send.

      No, there isn't a way to automatically resend them without opening and clicking Send. You could probably use a macro, but I don't have one that does that.

  119. Jean says

    I've created the messages on my old PC (that has no internet), exported the Outbox file, and then imported them into my internet-enabled laptop. I did that because the Mail Merge on the laptop doesn't work, while the Mail Merge on the old PC works.

    Thanks, Diane, I'll try to find such a macro, hopefully there is one.

    • Diane PoremskyDiane Poremsky says

      I'm guessing they were marked as read by the import process - but it could be a problem with the account not matching up correctly. This would be more likely to work: copy the pst to the other computer, add it to the outlook profile and set as default - then do a send/receive.

      This macro should work on messages that need to be resent from the outbox. It should send all but possibly the selected message (that's an outlook bug, not the macro.)

      Public Sub SendDrafts()
      Dim olApp As Outlook.Application
      Dim NS As Outlook.NameSpace
      Dim SendMail As Outlook.MAPIFolder
      Dim Drafts As Outlook.Items
      Dim DraftItem As Outlook.MailItem
      Dim lCount As Long

      Set olApp = Outlook.Application
      Set NS = olApp.GetNamespace("MAPI")

      Set SendMail = NS.GetDefaultFolder(olFolderOutbox)
      Set Drafts = SendMail.Items

      For lCount = Drafts.Count To 1 Step -1
      Set DraftItem = Drafts.Item(lCount)
      DraftItem.Send

      Next lCount

      Set SendMail = Nothing
      Set NS = Nothing
      Set olApp = Nothing

      End Sub

  120. Kathryn Salm says

    Yeah! I have Outlook 2010 on Windows 7 and had a stuck too large e-mail in the Outbox that was causing all kinds of issues. I tried the delete message out of the search box and that didn't work. But, when I went "offline" - waited - then came back it deleted perfectly! Thanks Diane! :)

  121. Marcus says

    Diane,

    I am in an enterprise environment. We use both Outlook 2010, and 2013, we will soon upgrade everyone to 2013. I am having a sporadic issue with email going to the Outbox, and it will not send, whether marked unread or not. I have to have the users logout of Outlook, then it force you to either cancel or cancel without sending. This isn't happening to everyone. Several people have this issues some more than others. I read on one document, that this is a known issue, and there is no real fix for it. Then it suggested a registry error. But the warning was, if you delete the wrong file you can corrupt your Outlook all together. This has been happening now for several weeks.

    Do you know a fix for this or a work-a-round? Thank you for your help.

    • Diane PoremskyDiane Poremsky says

      I would try two things: disable all addins that we're being used and if the problem continued, try a new profile.

  122. Umeshwari says

    My outlook is not properly working mails are stuck in outbox. I have done all the known troubleshooting , repair. But not worked at all.

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