Volume 30 Issue 22

Issue Date: July 3, 2025 « Previous Issue | Next Issue »

The following articles were included in our Exchange Messaging Outlook (EMO) newsletter published on July 3, 2025.

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Today's Highlights »

Urban legend: Microsoft Deletes Old Outlook.com Messages
Classic Outlook Calendar and "Add a service" Error
New Phones and the Authenticator App

Urban legend: Microsoft Deletes Old Outlook.com Messages

I frequently see questions posted in the forums where users say Microsoft is deleting their older messages. The times vary, from 2 years, to 5, 10 and even 20 years.

The user insists it is a Microsoft policy to delete old mail. It is not. Microsoft won’t delete mail even if your mailbox is over quota; they’ll bounce incoming mail and not allow you to send mail instead.

The messages always go something like this:

"I’ve been using my Hotmail account daily for [nn] years. I was looking for an old message from [year] and only have mail going back to [year2]. Does Outlook.com automatically delete my emails from before [year2]? I can’t find any information that outlook.com has a policy to delete emails based on age or size. "

You can't find a policy because there is none. Microsoft does not delete old email from user’s mailboxes, with two exceptions. The exceptions are: from your Deleted Items and Junk email folders (and only from those two folders) and if you don’t log in at least once a year (used to be 270 days years ago).

If you don't log into outlook.com (and separately to onedrive.com) at least once a year, the mailbox (and OneDrive) will be purged of all files. (Logging in the two servers using apps counts as logging in.)

If you are missing older mail from around 2008 and earlier, possible causes are:

1. You deleted it yourself.

2. Your mailbox was full, and you deleted or archived the mail using POP3. Until around 2008, outlook.com mailboxes were a puny 500 MB. That is not much for mail, calendar, and contacts, especially if you had the account since the early days of Hotmail. When Microsoft moved Outlook.com to Exchange online servers in 2016/2017, mailboxes grew to 15 GB.

3. You used a POP3 client. Years ago, many POP clients, including Outlook, defaulted to delete mail from the server as you downloaded it using POP3. Now most (if not all) now default to leaving it on the server for 14 days. (If you used POP3 and have the old data files, the mail can usually be recovered from the files.)

4. You went more than 270 days without logging in. Back then mailboxes were purged if you didn't log into the account.

If you ever used classic Outlook, using either the older Outlook Connector or a newer client using Exchange services, to connect to your mailbox, was auto archive enabled? Auto archiving will remove mail from the server as it ages. Default was to archive mail and calendar at 2 years, but configurable up to 5 years.

If you use a current version of classic Outlook and older mail is not syncing to Outlook, check your sync slider settings. To save hard drive space, Outlook may default to syncing less than all of your mail. Go to File > Account Settings > Account Settings. Double click on the account to view or change the sync slider.

Classic Outlook Calendar and "Add a service" Error

In recent weeks, users are receiving an error when try to create a new event or open and existing event in classic Outlook. The error dialog is for "Add a service." The message says "We couldn't find a work or school account with that email address." while displaying the correct personal Outlook.com email address in the dialog.

Microsoft is investigating and believe this will be fixed soon, but in the meantime, you can stop the messages by disabling Connected Services. Note that this will also block other services you may be using, such as templates and spell check.

Open File > Office Account
Click Manage settings button (it's just under your name and email)
Uncheck Connected Experiences in the dialog.

New Phones and the Authenticator App

If I sound like a broken record or a nagging parent, it’s because I hate seeing people lose their email accounts and I hate being the bearer of bad news.

"I got a new phone 2 days ago. I forgot to transfer my information to the Microsoft Authenticator application while transferring my information. And since I always log in with a code, I can't log in now."

Unfortunately, the user is going to lose their account if they don't have another method to authenticate: Support cannot help you get back into the account.

Sadly, this question comes up multiple times a day in Microsoft forums and Reddit. Microsoft support cannot help them gain access to their account. They cannot reset their password or recover their account.

If you are using the authenticator and are getting a new phone, you must verify you have other forms or authentication or have the authenticator set up on the new device before you wipe and return the old device. Check your verification proofs here: https://account.live.com/proofs/manage/additional

If the authenticator is your only method of authentication, you will lose the account if you don’t have the phone it is setup on.

If you use SMS for authentication and get a new phone number, you will not be able to authenticate. You need to add the new phone to your account before you lose access to the old number.

Microsoft and Google allow you to set up multiple forms of authentication. If you have more than one mobile device (phone and tablet), set up the authenticator on each device. Add email addresses that are checked often, and you are unlikely to lose access to. If Windows asks you to set up Windows Hello to log in, say yes.

While you can backup the Microsoft authenticator, in my experience, it only remembers the accounts, you need to set up the authentication again for most accounts. (Kind of useless, if you ask me.) You need multiple forms of authentication, and you need to keep them updated in you get a new phone number or email address.