Outlook signature issues after Office 365 upgrade

Question

I recently upgraded my local instance of Office 365 from version 16.0.15225.20204 (2205) to 16.0.15831.20190 (2211). Since doing that I am experiencing issues with my preexisting signatures in Outlook. I had three signatures, one of which was being used as my default for all new messages. After the upgrade, all of the signatures are present in the drop down menu and are able to be used. If, however, I go into the "Signatures..." menu item, the only signature I see is the one I had as the default for new messages. This prevents me from selecting an already created signature as my new default for either new messages for replies/forwards. I also can not delete the other signatures because they doesn't appear in the list. If I try and recreate either of them with the same name, Outlook says I can't because that name is already in use.

When I go to the directory where the signatures are held, all of the files are there, but with some changes. The default signature files now have my email address appended to the corresponding file names and folder name. The .html file for that signature also has a new date/time stamp. The files for the other signatures remain unchanged. There is a new folder called "Archive", which contains the original copies of the files and folder for the default signature.

What has obviously happened is that the upgrade also triggered an upgrade for my signature, but it only did it for the one that was selected as the default for new messages. This did so without warning or information about what the effects would be. The problem is that the administration of any of the non-default signatures would require me to recreate those signatures by copying the contents, manually deleting the files and then creating new instances of those signatures. That brings up several questions:

1. Is this behavior expected after this upgrade?
2. Is there a way to prevent this from happening as part of the upgrade?
3. If this is unavoidable, is there a way to address this within the Outlook interface that doesn't require manipulating the files directly?

Thank you for any feedback on this situation.

Answer 1

Dear KMM357,

Good day! Thanks for posting to Microsoft Community.

Based on your description, we understand that you have a concern with Outlook signature issues after Office 365 upgrade.

Firstly, may I please confirm if you are using Outlook for PC?

If so, there is a new feature rollout called Outlook roaming signatures. This feature helps to roam email signatures in Outlook for Windows across devices. Previously, signatures were stored locally on user's device, and if a user wanted to have their signature be the same on different devices, they had to recreate the signature on each device. As a part of this change, signatures will now be associated with email accounts. signatures will be stored in the user's mailbox, and they will be available on all devices where that account is configured. Users don't need to do anything to enable the new feature, as it will become effective automatically.  For additional information you can refer to Outlook roaming signatures - Microsoft Support.

The Outlook roaming option is enabled by default, so if you need to disable, you can follow the below steps:

You can refer to Outlook roaming options - Microsoft Support for more details.

Removing the 'Store my Outlook settings in the cloud" might give you the ability to make changes. Kindly also check whether the signatures are stored in the 'Signatures on this device', which might be why there are duplicates.

Just in case you have any further queries, or I got you wrongly, please let me know and will gladly get back to you.

Thank you for your precious time and have a nice day.

Best Regards,

Ashraf | Microsoft Community Moderator

Answer 2

Thank you Ashraf. Yes, I am using Outlook for PC. I do see the setting to disable roaming options. However, disabling this option doesn't resolve the issue. All of the signatures are usable on the local device, but they are not manageable. The only way they are manageable is if I delete the ones that aren't the default one and then recreate them. Ultimately the question is, if you have more than one signature and you sign into Outlook for PC after an update, how do you make it so that ALL of the signatures will get stored in the cloud? Not only did it not do that automatically, a person would have to go into the directory where the files are and manually delete them in order to recreate them for them to get stored on the cloud. Is there another way to do this?

Answer 3

Dear KMM357,

Thank you for the response.

With the upgrade, since signatures are stored with the user's mailbox, it is necessary to associate signatures with specific accounts. When this feature is enabled, Outlook reads the existing local signatures, then copies copy signatures selected as default for new messages or Replies/forwards to that account's mailbox.

Other signatures do not roam and continue to be available locally on the device under the email account Signatures on this device. This might explain why not ALL signatures are stored in the cloud. These local signatures should still be available for use during email editing by selecting Message --> Signatures but cannot be edited unless they're associated with one of your existing email accounts. 

However, since this feature is still in the roll out phase according to the Microsoft O365 Roadmap. I think it might be too early to draw a final conclusion. You can however always give your feedback through the Outlook app or in Outlook · Community (microsoft.com).

My apologies if I got you wrong in anyway and for any inconveniences caused.

Have a great day ahead.

Best Regards,

Ashraf | Microsoft Community Moderator.

Answer 4

One of the issues i'm having is that it's not even populating them in the choose default signature area of the new outlook.

Even when I disable the cloud settings its almost like it's not looking in the \Roaming\Microsoft\Signatures folder anymore.

Any suggestions?