Follow up Flags in Outlook 365 are randomly disappearing - Please Fix

Question

Follow-up flags on emails in Outlook 365 are randomly disappearing!  They will initially show up correctly, but seconds after the message is sent, the follow-up flag will disappear.  This happens 10-50% of the time when I send an email that I flag for me to follow up.  Here is what happens:

1. When I draft an email and choose a date for follow up, the message (before I send it says) "After this message is sent, it will be flagged for you with the following information...", as one would expect.
2. Once the message is sent, for the first 5-10 seconds after sending, everything looks right. The message shows up in the tasks list for me to follow up on, it is highlighted yellow in the Sent Items folder, and if you open the sent message it says that it has been flagged for me to follow up on whatever date I chose.
3. After 5-10 seconds, the message will disappear from the tasks lists, no longer be highlighted yellow in the Sent Items folder, and when you open the sent message, it only says "Recipient received: Follow up".  I have watched this happen numerous times.

Sometimes steps #2-3 don't even happen, and the email is just never flagged for me to follow up once it is sent, and only says "Recipient received: Follow up" when you open it in the sent items folder.

This leads to numerous emails that need to be followed up on being missed. This is a long-standing bug in Outlook, currently occurring for me in Outlook 365 ProPlus on Windows 10 Pro and previously having occurred on an older machine with Outlook 2013/Windows 7 as well as on the current machine with Outlook 2016/Windows 10. It is clearly not a problem with a particular Outlook install or mailbox instance.

Please fix this?!  It makes follow-up flags basically unusable because they are so unreliable. Someone once suggested updating from Outlook 2016 to 365 so that the application is always up-to-date, but I have done that and it did not resolve the problem.

This has been reported numerous times before, and no solutions have fixed the problem: 

• https://answers.microsoft.com/en-us/msoffice/forum/all/flag-for-follow-up-automatically-switches-from-for/ae10cea7-0349-4b88-9816-c169f5581cf4 and
• https://answers.microsoft.com/en-us/outlook_com/forum/oemail-ocleanup/flag-for-follow-up-automatically-switches-from-for/43018143-82f7-4632-8638-02f052887313
• https://answers.microsoft.com/en-us/msoffice/forum/all/disappearing-follow-up-flags/82f77b11-4a6c-e011-8dfc-68b599b31bf5
• https://answers.microsoft.com/en-us/msoffice/forum/all/follow-up-flags-deleted-after-sending/00c6ec35-02b1-4c2b-a3e0-6f9f1110cef2
• https://answers.microsoft.com/en-us/msoffice/forum/all/outlook-2016-flags-for-me-and-reminders-disappear/598a83b1-4de1-4da3-a84a-f92550d4a0d8
• https://answers.microsoft.com/en-us/msoffice/forum/all/follow-up-flag-on-sent-items-just-suddenly/48acccd9-4a27-456a-9c8b-ff8961a3d5f2
• https://answers.microsoft.com/en-us/msoffice/forum/all/flags-in-outlook-2010-disappear-after-applying/71b4eda6-924e-4dcf-b9ee-25f78271d075
• https://answers.microsoft.com/en-us/msoffice/forum/all/flag-email-for-follow-up/deb42532-7194-4ba7-a1e8-8e43f1f76f88
• https://answers.microsoft.com/en-us/msoffice/forum/all/flag-for-follow-up-automatically-adding-flag-for/c0013e2d-5b3e-4468-9e94-f10199395450

Answer 1

Hi Anna,

I have the same issue.... for years

Outlook365 w/Outlook 2013 and 2016

Please help restore my confidence in Flags

This is one of the most important features in my eyes.

Thank you in advance,

Dror

Answer 2

Hi Anna,

I have the same issue.... for years

Outlook365 w/Outlook 2013 and 2016

Please help restore my confidence in Flags

This is one of the most important features in my eyes.

Thank you in advance,

Dror

This was incorrectly marked as an answer to this question... it is still not resolved.

Answer 3

Hi Alison - Did you ever get this resolved? I'm having the same issue. It doesn't happen every time, but enough times for me to forget to follow up on certain matters.

Answer 4

Hi Alison - Did you ever get this resolved? I'm having the same issue. It doesn't happen every time, but enough times for me to forget to follow up on certain matters.

No, unfortunately it has not been resolved.  Anna from Microsoft messaged me to say “According to the issue symptom, after consulting, since we have limited access to troubleshooting tools and related channels, we suggest you contact your organization admin and let them open a Service Request at Office 365 admin center (https://admin.microsoft.com/Adminportal/Home?source=applauncher#/homepage). There’s our dedicated team and they will further assist you working on the issue.”

But my organization isn't able to pursue this troubleshooting service request option (frustratingly), so I seem to be at a dead end.  If anyone is able to pursue further troubleshooting in this way, I highly encourage it!

In the meantime, all I can do is semi-regularly submit "I Don't Like Something" feedback within Outlook to report that this problem persists - and I encourage you all to do so as well.  Perhaps one day someone will do something about it.

Answer 5

Hi Anna,

Thanks for getting back to me and looking into this, I very much appreciate it.  It is certainly a sporadic issue; I might send 10 emails in which the follow up flags behave normally, and then three emails in a row will all have this problem.  Or every other email for a whole day will have the problem. For a while I kept a log of every email that was flagged incorrectly, but there was no pattern.

Office 365 is already updating automatically so everything can be as up-to-date as possible.

I currently have the same version as you: Version 1909 (Build 12026.20344 Click-to-Run).

This probably has persisted across multiple version of Outlook - currently Outlook 365 ProPlus on Windows 10 Pro and previously on an older machine with Outlook 2013/Windows 7 as well as on the current machine previously running Outlook 2016/Windows 10.

I understand it may be hard to troubleshoot if the issue is not reproducing itself for you, but I hope you can see by the number of people who have reported this that it is a real, long-standing issue.

In the To-do link that you sent, the "Flagged Email" option was already toggled for me.

Thank you again for the assistance, and kind regards,

Alison