Volume 31 Issue 1

Issue Date: January 15, 2026 « Previous Issue | Next Issue »

The following articles were included in our Exchange Messaging Outlook (EMO) newsletter published on January 15, 2026.

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Today's Highlights »

What’s Deleting My Mail?
Using iCloud with ARM-based Processors
Update: Error Opening iCloud Appointments
Find Attachments Opened from Classic Outlook
Coming Soon: Open Templates in Outlook Mobile

Due to family responsibilities in real life, Exchange Messaging Outlook will be published every two weeks for the time being. If there is any important information that needs to go out between issues, I'll send out a special edition.

What’s Deleting My Mail?

I had two clients last week whose mail was getting deleted or moved to the junk mail folder as it was downloaded.

While Outlook could be responsible for moving messages to the Junk Mail folder, it’s always a badly written rule that is deleting messages. The exception is using the Junk mail filter in classic Outlook to delete suspected junk email. That was a bad option from the time it was added to Outlook and should never be enabled. Fortunately, new Outlook does not have an option to delete suspected junk mail.

For Junk email: first check the Junk mail settings and the blocked list. Classic Outlook should be set to “No Automatic Filtering. Mail from blocked senders is still moved to the Junk Email folder.” As the junk mail filter hasn’t been updated in about 10 years, using the no automatic filtering option is highly recommended. Never use “Permanently delete suspected junk email instead of moving it to the Junk Email folder”. Junk Email options is accessible from the Home tab > Blocked menu (in the Delete group) > Junk E-mail Options...

New Outlook (and Outlook on the web) have two Junk mail options: Standard and Strict. Strict will move messages from people not in your safe list and contacts to the Junk Mail folder. This is in View tab > View settings > Mail > Junk email.

Check for Rules, for both moving to the junk email folder and deleting messages. Pay special attention to any rule that uses words in the subject or body. Adding common words or abbreviations that could be the start of a word (such as “acc”, which will also apply to “according”). If you need to look for partial words, add a space at the end: "acc ". This way the filter will look for whole words in the middle of sentences but will miss words at the end of a sentence or subject (because they won't end with a space.)

Adding addresses to the Safe list won’t help if a rule is moving the message. It also won’t help if a filter on an IMAP server is moving the messages to the Spam filter. Safe (and Blocked) senders is applied to mail as Outlook downloads it to the Inbox.

Using iCloud with ARM-based Processors

Users with computers running ARM CPUs (such as Surface and other Windows computers, or Parallels on MacBook) cannot sync calendar and contacts to Outlook using the iCloud app. The iCloud app installs and installs the Outlook iCloud add-in but the selection for calendar and contacts is not available.

This is something Apple needs to fix, and supposedly they are working on it, but in the meantime, affected users have two options. They can either use new Outlook or gSyncit to sync the iCloud calendar and contacts.

If you only use the iCloud calendar or use the iCloud contacts with an iCloud email account, new Outlook is a good option if you don’t need other features found only in classic Outlook.

However, new Outlook doesn't currently share contacts between accounts. If you use iCloud as your master contact list for other accounts, using gSyncit is a better option. It’s not free but a license is not expensive.

Another option is putting the calendar and contacts in a Microsoft account, either Outlook.com or a business account, and turn off sync for iCloud calendar and contacts on your devices. I only recommend this if you are using a Microsoft account for email, as you need to add the account to Outlook and your mobile device.

Update: Error Opening iCloud Appointments in Classic Outlook

As I mentioned in the EMO back in August 2025, users are receiving the following error message when they try to open iCloud appointments synced to classic Outlook.
“To help prevent malicious code from running, one or more objects in this form were not loaded.”

The fix was to change the ActiveX settings in Word’s Trust Center: In Word, open File > Options > Trust Center > Trust Center Settings > ActiveX Settings. Select “Enable all controls without restrictions and without prompting (not recommended; potentially dangerous controls can run) controls”. Also enable “Safe mode (helps limit the control’s access to your computer)”.

Changing that setting could leave the user at risk if they opened an infected document.

Instead of changing that setting, you can try editing the registry, removing Apple subkeys in two registry keys.

Disable the iCloud add-in in Outlook and close Outlook or sign out of the iCloud add-in, which removes it from Outlook.

Then open the registry editor (start typing registry editor on the start menu, open it when it comes up).

Browse to HKEY_CURRENT_USER > Software > Microsoft > Office > Outlook > FormRegions
Here you might find the following subkeys. If so, right-click on each and choose Delete.
Apple.DAV.Appointment
Apple.DAV.Contact
Apple.DAV.Task

Next browse to
HKEY_LOCAL_MACHINE > SOFTWARE > Microsoft > Office > Outlook > Addins
Delete the Apple.DAV.Addin subkey and any other Apple.Dav subkeys that might be there.

Rebooting may not be necessary but is recommended. Then either enable the iCloud add-in or sign back into iCloud.

Find Attachments Opened from Classic Outlook

A client called me in a panic a couple of days ago. He opened an attachment in Outlook, edited it then closed it. He wasn’t sure if he saved it but couldn’t find it.

When something like this happens, you can check Outlook’s SecureTemp folder. Attachments opened from Outlook are written to the SecureTemp folder so your antivirus software scans it. Outlook will delete the attachment if you close it before selecting another message. But if you leave it open and switch to another message, Outlook will leave it in the SecureTemp folder. Changes will only be saved to the file if you clicked Save (or pressed Ctrl + S).

The quickest way to check the folder is to open File Explorer, type shell:cache in the address bar and press Enter. This will open the temporary internet cache folder, which contains a subfolder named Content.Outlook, where you'll find a subfolder with random characters for the name. This is where Outlook stores attachments you opened from an email. You shouldn’t need to change the View settings to Show hidden folders to see the Outlook folder. Since this is just a temporary files folder, you can delete the files that are in the folder, or delete the folder. Outlook will create a new folder when you open an attachment.

If you were working on a Word document or Excel file, you can check for Unsaved files in the application ‘s File > Recover Unsaved Documents or from File > Open > Recover Unsaved Documents. They are at the bottom of the page, under the recent files list.

Coming Soon: Open Templates in Outlook Mobile

From the Microsoft 365 Roadmap: Open and Send Outlook File Templates

In February, Microsoft will begin introducing the ability to open and send OFT files (Outlook File Templates) on Android and iOS mobile devices. When this is available, users will be able to view and open OFT files as a draft message then send.