Office 365 keeps sending messages to Junk mail

Hello everyone,

one of our clients has recently moved their user's email accounts to Office 365.
One of the users has problems with emails consistently ending in Junk mail despite trying to force it on the whitelist, add to safe senders etc.
The weird thing is that she is a part of a distribution list named "tickets@company.com" - the company gets generated emails from their ticketing system or customers inquiries to that specific delivery group and everyone else gets them in their inbox or the TICKETS folder that they have made it for separating these generated emails, only she gets it directly to the Junk folder. Occasionally they do get in the inbox but after a few minutes, they get moved from the inbox to the Junk folder. Also tried changing in the webmail version of the 365, adding to whitelist, disabling junk mail all together but nothing helps.
 It all started a couple of weeks ago, all of sudden she just got about 1000+  old, deleted emails reappear in the junk folder...

Anyone had any idea what to do, try out?

Thnx in advance!
Marin BarisicAsked:
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

x
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

David FavorLinux/LXD/WordPress/Hosting SavantCommented:
Keep "unjunking" + replying to these email + eventually the problem will likely clear up.
David Johnson, CD, MVPOwnerCommented:
with this history I would think that another application is doing the moving.. especially the deleted messages re-appearing
Marin BarisicAuthor Commented:
Thanks all for trying to help.

1. The user keeps unjunking for over two weeks now and nothing changes, will keep on doing it
2. We thought the same, so a completely new Windows 10 system was bought and installed, even Office 2016 Home and Business was installed with a retail licence key instead of installing it from the Office 365 account. The only thing that is still the same is that the account is merged to an Office 365 account, so my guess would be nothing we try works on the client side, could it somehow be on the server side? The company doing the migration to 365 and the administrator that actually added the users to the domain are a little of help in this situation.


Would it be possible that, somehow, these settings (to send these messages to junk) are somehow applied on the server side, something else than what user sees and is able to modify when logged Outlook 2013, 2016 or to web office 365?

thnx
Big Business Goals? Which KPIs Will Help You

The most successful MSPs rely on metrics – known as key performance indicators (KPIs) – for making informed decisions that help their businesses thrive, rather than just survive. This eBook provides an overview of the most important KPIs used by top MSPs.

Andrew LeniartIT Consultant & Freelance JournalistCommented:
Marin,

I've read over all your comments, and the other expert's comments, and the only thing that's making any sense to me is David's guess that another app could possibly be doing the moving.

Let's go back to basics for a moment and cover "all" possible bases that I can think of. Following all the steps below "should" work.

Note: To confirm the correct problematic email address which is being sent to junk, click reply on one of those messages - the email address that appears in the To: field of the reply message is the one you will need to add in the steps below.

On the locally installed copy of Outlook 2016

Add-ins Options

Launch an elevated copy of Microsoft Outlook (Right click the Outlook icon and select "Run as administrator") and disable ALL non standard add-ins found in  FileOptionsAdd-ins. If you're not sure which ones are standard and which ones aren't, disable them all, or post what you have in there here and we'll advise.

Junk Email Options

1. Go to the Home Tab, click JunkJunk E-mail Options...

2. On the Options Tab, select No Automatic Filtering

3. On the Safe Senders Tab, ensure the problematic email address is entered in this list. If not, add it. Ensure that "Also trust email from my contacts" is also ticked.

4. Add the troublesome email address to the Safe Recipients Tab.

5. Ensure the troublesome email address has not been entered on the Blocked Senders Tab.

6. On the International Tab, click the Blocked Top-Level Domain List button, then click the Clear All button, then click OK

7. Still on the International Tab, click the Blocked Encodings List button, then click the Clear All button, then click OK

8. Click OK to close the June Email Options box in Outlook.

Still in Microsoft Outlook local Install

1. On the Home Tab, click RulesManage Rules & Alerts

Any rules configured there? - If yes, turn them all off for now. (Untick them)

2. Click the OK button to close the Rules and Alerts window.

That's it for the locally installed copy of Outlook.

Now in Outlook Online (OWA) - Check the following;

1. Click the Cog to the top right of your browser, then click OptionsMailAutomatic ProcessingInbox and sweep rules - Anything in there? If yes, disable or clear them and Save changes

2. Click MailJunk email > Blocked senders - Ensure the problematic email address or domain does "not" exist there and Save changes

3. Click MailJunk email > Safe mailing lists - Take careful note of the information at the top, as quoted below. (Important in your scenario)

Messages with mailing lists often have an address other than your email address on the To line. If you want to receive an email from a mailing list, add the address of the list you trust to the box below, click the (+), then click save.

Ensure the address on the To: line of the messages being junked that she is getting, has also been entered here and save.

4. Click MailJunk emailSafe senders - Ensure the problematic email address is entered here and save.

5. Under GeneralManage add-ins - Ensure there are no non-standard add-ins there. Disable any there that you're not certain about. If you're not sure, again, post what is listed there and we'll advise.

Now test again.

All of the above steps cover every possible cause that I can think of to do with Junk Email handling. It has to work! :)

If you follow the listed steps and the problem is still not resolved, I'd be looking at third party programs installed on the system. AV, Anti-Malware etc.

Let us know how you go.

Regards, Andrew
Gopi RajuSystem EngineerCommented:
Since this is happening to only a particular user i would suggest to check the users inbox rules and see if there is any rule configured for moving the mails to junk.
Marin BarisicAuthor Commented:
Hey Andrew,

thank you very much for your detailed reply!

I have tried the steps you mentioned and it did not work, I think...

What happened is when I did this step:
Still in Microsoft Outlook local Install

1. On the Home Tab, click Rules > Manage Rules & Alerts 

Any rules configured there? - If yes, turn them all off for now. (Untick them)

Open in new window

the client version of Outlook 2016 pulled about 800+ emails from somewhere and put them in Deleted items.

When I tried editing the OWA there were no emails in the account, the problem is when I am asked on the login page where to log in I got two options: 1. the work or school account and 2. the personal account.  I am only able to access the personal account (the empty one), for the work or school account I get the wrong password and when I try to reset it, it notifies me that the password can not be changed as it needs to be changed by the administrator and I could only notify the administrator through that message.

EDIT: I am able to see the emails only in outlook.office365.com, I will try your suggestion of the OWA setup there now..

To me, it seems like there are parallel issues here, the client email was originally on a local exchange - then it was moved to office365 together with all accounts in the company and now can only be administered by the administrator that did the migration. Currently, there is installed Office Business and Home 2016 retail version but the account is on Office 365, could this be the problem? It seems like all changes made on the local Office Business and Home 2016 retail do no propagate to the OWA of 365 and somehow there is a mixup. So when the local Outlook pulls the emails it gets them re-configured afterward when it syncs with the OWA 365 and puts them in junk, does this make sense?

Thnx
Marin BarisicAuthor Commented:
Another question,

could I just disable the junk email filtering in 365OWA and then configure everything on the Client side in H&B2016?

UPDATE2:

Now I found in OWA365 in GENERAL - MANAGE ADD INS - "ACTION ITEMS" is clicked. It says, among other things, it will "read, create and update emails in my inbox" and it is checked

Could this be the culprit?:)
Andrew LeniartIT Consultant & Freelance JournalistCommented:
the client version of Outlook 2016 pulled about 800+ emails from somewhere and put them in Deleted items.
Just viewing Rules and Alerts does not do that, so either rules were run that caused this to happen, or the 800+ email occurrence happened by coincidence when you were viewing rules. You neglected to mention whether or not there are any rules configured in the Local Outlook client or OWA. Are there?

From what you've just said, I'm starting to suspect there is another Account configured in Outlook 2016 that you don't know about.

What do you see when you click FileAccount SettingsAccount SettingsEmail in Outlook 2016 (Local install) ? How many accounts are configured in there?

Also, look at FileAccount SettingsAccount SettingsData Files in Outlook 2016 local install? What is currently in there?

Post a screenshot if easier and just blur out any identifiable information.

was originally on a local exchange - then it was moved to office365 together with all accounts in the company and now can only be administered by the administrator that did the migration.

Ahh the plot thickens. :-) The question now is was the migration completed correctly and sucessfully? Were the old accounts corerctly retired after migration? Those 800+ messages had to come from somewhere, so if they're not visible in OWA, then Outlook "must" be connected to another server source.

Are you able to contact the administrator who performed the migration? There could be rules and settings in effect here that are leftover from the local exchange server install. If that's the case, then things are starting to make more sense because just dealing with the mail being redirected to the junk folder in outlook isn't adding up here if all the settings I've suggested were followed.

Currently, there is installed Office Business and Home 2016 retail version but the account is on Office 365, could this be the problem? It seems like all changes made on the local Office Business and Home 2016 retail do no propagate to the OWA of 365 and somehow there is a mixup.
Couldn't be the problem if those same messages are not propagating back to Exchange server. Please check and advise how many email accounts are configured in Account settings and also what data files are currently on the machine.

I'd suggest forgetting about OWA for now if Outlook is not synchronizing with 365 anyway and concentrate on getting those emails to stop being dumped to junk whenever they arrive. Ie: Disregard the OWA instructions I gave for now. They can be done later if need be. I gave the OWA steps for the sake of completeness, but I was under the assumption that there was only one email account and one source server being dealt with here. With the revelation of a second local exchange server being in the mix, along with a recent migration on top of that, things could be a little different. Need to step through this slowly.

Get back to me with Account Info (how many accounts configured and what types of data files Outlook is using and we'll go through it slowly. Also try to contact the Administrator who performed the migration - check to see where those 800+ email messages that don't exist in O365 could have gotten to your local install.
Andrew LeniartIT Consultant & Freelance JournalistCommented:
Now I found in OWA365 in GENERAL - MANAGE ADD INS - "ACTION ITEMS" is clicked. It says, among other things, it will "read, create and update emails in my inbox" and it is checked
Could this be the culprit?:)

Highly possible, yes. I don't have it in mine, but it can be enabled as a default setting by your Administrator. Uncheck it and see if that helps. I think you may have found your culprit, but now I'm confused as you indicated Outlook was not synchronizing currently.

Are you getting the problematic emails to Outlook locally, on OWA, or on both?  Please clarify.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
Andrew LeniartIT Consultant & Freelance JournalistCommented:
could I just disable the junk email filtering in 365OWA and then configure everything on the Client side in H&B2016?

Sorry, forgot to answer that one. The answer is yes. :)
Andrew LeniartIT Consultant & Freelance JournalistCommented:
I think it's actually preferable to do it that way and configure all settings locally - though others will likely disagree :)
Andrew LeniartIT Consultant & Freelance JournalistCommented:
Are you getting the problematic emails to Outlook locally, on OWA, or on both?  Please clarify
Oh yes, and if on both, do they end up in Junk mail on OWA as well as your locally installed copy of Outlook?
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Microsoft Office

From novice to tech pro — start learning today.