Junk emails flagged

@Betty Bauer said

Hotmail junk emails are flagged and put in Flagged folder on the Mac.

I am not aware of a standard "Flagged" folder in Outlook. Do you perhaps mean you see these emails when you filter you messages by "Flagged"?
https://support.microsoft.com/en-us/outlook/how-do-i-sort-my-inbox-by-unread-flagged-starred-or-attachments

If possible, a screen shot of what you see when using your Outlook for Mac would be helpful. Once you take the screen shot on your Mac, you can Paste it into a new comment here.
https://learn.microsoft.com/en-us/answers/support/attachments#copy-and-paste-or-drag-and-drop

I am having essentially the same problem as Betty. I too have a MacBook, and in macOS Mail (and the various iOS accessories) there is a Smart Folder called "Flagged". It searches for any email that has the "flag" attribute set, the little red flag in Outlook.

The problem is not the Flagged folder - that is doing what it does, which is find anything in the system that is flagged. The problem is that all messages in the Junk Mail folder are being flagged - whether spammers have started sending messages that way, or whether something in Outlook is causing all Junk Mail to be marked as flagged, that I cannot say.

I personally tried setting a rule "For all Messages -> Mark with Importance 'Normal' + Clear Flags + Clear Categories" but it's still missing a few messages here and there.

So the base problem is in the Junk Mail folder and it marking all messages as flagged. It's been going on for a week or two at this point and frankly it's getting pretty irritating. Hope we can find a solution!

@Miguel Segimon said

in macOS Mail (and the various iOS accessories) there is a Smart Folder called "Flagged"

1 -- Are you refereeing to an Apple Mail Smart Mailbox with a Condition of Message is flagged?

all messages in the Junk Mail folder are being flagged

2 -- If you move a normal message to the Junk folder, or Report/Mark it as Junk in Outlook, does the message get flagged when it moves to the Junk folder?

On my MacBook, the inboxes include a Flagged folder as well as a Junk Email folder. The emails going to Junk Email are now flagged

I wonder if spammers are sending the emails with flags? In my MacBook mailboxes, the Outlook junk emails go to Junk and also those same emails are already flagged and in the flag folder.

@Betty Bauer said

The emails going to Junk Email are now flagged

If you move a normal message to the Junk folder, does the message get flagged when it lands in Junk?

If your Outlook for Mac has the Report -> Junk menu choice, and you Report as Junk a normal email, does the message get flagged when it is moved to Junk?

If I move a new Hotmail email from the Inbox to Junk on my MacBook, it does not get flagged. Junk mails coming to my MacBook automatically go to the Flagged folder as well as the Junk folder.

@Betty Bauer said

I wonder if spammers are sending the emails with flags?

Possible, but no way to know for sure without examining one of the spam emails in detail, to see if a MAPI or IMAP flag property was already assigned when it first arrived in your mailbox. Not something we can do via a forum exchange.

You might want to bring in Microsoft Support so they can examine one of the spam emails and your Outlook environment.

If you have a qualified MS 365 Subscription:
https://learn.microsoft.com/en-us/microsoft-365/admin/get-help-support

Otherwise, free Mac In App Support
https://support.microsoft.com/en-us/office/contact-support-within-outlook-for-mac-d0410177-8e65-4487-93f7-206a3a3d71a8

@Betty Bauer said

If I move a new Hotmail email from the Inbox to Junk on my MacBook, it does not get flagged

Thank you for the report. I am afraid that you are going to need Microsoft Support to find the cause for this issue. (See my previous comment).

Same symptoms for me as with Betty - I moved a message from the Inbox to the Junk Mail folder and it did not get flagged either. I do have an M365 sub, so I will see about the tech support avenue, although I may try a couple more tests before doing so.

One that occurs to me is turning off all Apple Mail (iPhone, iPad, Mac) connections to hotmail and waiting for another mail or two to arrive in the junk mailbox and see if they get flagged. I can check on the web client. If they do get flagged, it's not Apple Mail. If they do not get flagged, that might indicate the MAPI or IMAP or whatever method we are currently using to connect is somehow enabling those flags.

Another thing to try is going to be updating to the latest macOS, which I think just released this week? If it's the client maybe the latest patch has a fix.

@Miguel Segimon said

may try a couple more tests before doing so

Excellent ideas. Please keep us posted on the results of your testing.

that might indicate the MAPI or IMAP or whatever method we are currently using to connect is somehow enabling those flags.

That was not the intent of my comment. I should have ask:

Do you get Junk email from more than one sender?

If so, do all your Junk emails, regardless of the sender, get flagged? (Means the Spammers are not causing it)

Yes, I get emails that are flagged from more than one sender. No, not all junk emails are automatically flagged. I click "Block Sender" and clear the flags before I delete the emails.

I believe every single email from senders of all stripes was getting flagged, regardless of sender.

It is possible that actual spam senders are all marking their messages as high importance and flag for followup; but there are some "legitimate" messages I send to junk anyway from what I'm going to call reputable sources that should not be getting sent with a flag on them. I was testing solving this with a rule - making Outlook remove flags and importance from every email that arrives, as I mentioned in my original response here. I have disabled that rule for now as it was partially successful - not fully, as there were still several emails that maintained a flag, but it will make it easier to answer the question we are posing - does every email have a flag.

IF every email going forward has a flag, even the "legitimate" ones, then there's something weird going on - because messages from this forum, which have not yet been allow-listed and land in spam for now, should NOT carry a flag on them, for example.

Not all junk emails are flagged... but, most of them I also get hotmail junk emails without flags that only go to my Hotmail Junk folder.

Ok, only "bad" spam is coming through with flags - "legitimate" companies that would likely listen to an unsubscribe request are not flagging.

So it looks like maybe Microsoft stopped stripping flags that it may have cleaned in the past?

-Miguel

Betty and Miguel,

Thank you both for the testing, I apologize if I'm getting the results confused.

But at this point can we theorize that only those emails that are marked as Junk by Apple Mail are the ones that are being flagged?

Have you completed the test where you remove the hotmail account from Apple Mail and see what happens to any new Junk?

No, apple mail has junk mail filtering completely disabled. There appears to be less emails being flagged in the last 24 hours, which makes me wonder if someone at Microsoft caught on and put in a partial fix. It used to be a straight zero. It became virtually every email from scam senders. Now it's only some of them.

Something interesting I noticed is that the emails are not just flagged, they are also marked as "high importance", or in applespeak, "High Priority". That I think is the key - on apple mail this shows up as a gray !! right next to the message title. I don't know if the messages are arriving with both a High Importance set and the flag set; or if they are arriving with High Importance and something in the queue (hotmail or Apple mail) is setting a follow up flag due to the high importance setting.

I just created a rule that tries to check for High Importance on incoming email and sets it back to Normal - I'll update my findings as the rule does its work (if it does work!).

@Miguel Segimon said

now it's only some of them.

I just created a rule that tries to check for High Importance on incoming email and sets it back to Normal

Thank you for the update. Please let us know the results of your new Rule.

I am sorry, but given the nature of this bug, I don't have any other suggestions on what you could try, other than bringing in Microsoft Support so they can examine your setup.

Mac In App Support
https://support.microsoft.com/en-us/office/contact-support-within-outlook-for-mac-d0410177-8e65-4487-93f7-206a3a3d71a8

No luck, the rule didn't accomplish anything. Messages are still arriving with a High Importance flag set, and for whatever reason Hotmail isn't stripping the flag - it could be something like the spam filter is throwing them in the junk box before processing rules, or the spammers are using some non-standard nomenclature for the high importance that hotmail is displaying but not filtering on.

As a temporary workaround on macOS mail I can create an alternate Flagged folder that searches for Flagged messages that are NOT in the Junk mailbox. Not sure if that's going to help on iOS devices, but one step at a time - I don't often use flagged on the mobile platforms anyway.

I'm getting more and more flagged emails each day.

Ok, smart folders somewhat solved the main issue, without touching the root cause which to be clear, is Hotmail is not filtering out scammers marking their spam messages as High Importance / High Priority.

On iOS nothing needed to be done - the Flagged mailbox on my phone does not look at Junk mail, full stop.

On macOS Mail I found two methods:

1. Simpler method:
   Go to the menu, Mail -> Settings -> General
   At the bottom of the pane unselect "Junk" from the "include results from" area.
   That will make the flagged smart mailbox stop reading from the Junk folder. Downside: it will not search Junk by default when trying to find messages in folders (which I do frequently as I have a very aggressive spam filter)
2. Trickier method: Hide the Flagged folder - right click on the folder, select "remove from favorites"
   Create a new Flagged folder - go to the menu, Mailbox -> New Smart Mailbox...
   In the pop up window create a Smart mailbox.
   1. Name: Flagged; Contains messages that match ALL conditions;
   2. Condition 1: "Message is flagged"; hit plus on the far right of the line;
   3. Condition 2: "Message is not in mailbox:" "All junk"
   4. Select "Sent Mail" if you want to find your own sent flagged messages.
   Once this is done, you will now have a new Smart Mailbox, but it will be hidden under the Smart Mailbox pulldown menu on the left. Pull that menu down, right click on the mailbox, and select "Add to Favorites". Advantage: if you want to get hits from junk mail when searching, you can keep that setting from the simpler method enabled, which is more flexible. Disadvantage: You lose the cool "Flag" icon next to the word Flagged, instead you now have the gear icon for a smart mailbox.

That's it!

This still does not solve the base problem of hotmail not filtering out incoming flags from scammers. Given the differences I've seen in a few days it's possible they're tweaking all that stuff. Figured I'd write this up in case other folks look for this solution in the future (including myself next time this bug bites me!).

Good luck @Betty Bauer and thanks for the assistance @Hornblower409 !

@Miguel Segimon said

This still does not solve the base problem of hotmail not filtering out incoming flags from scammers

Good stuff. Thanks. But ...

I am not seeing any other reports of this problem, here or in the Outlook Reddit forums. If the Spammers have come up with a new trick to get the Microsoft mail servers to pass thru the Flag and Importance properties, I would think that there would be more reports. And at least some reports from people who aren't using Apple Mail.

In my opinion, at this point, there are just not enough reports to draw any conclusions about the root cause.

Again, I would suggest that you bring in Microsoft Support so they can examine an actual environment that is experiencing the problem.

It looks like we have another report of this issue. User also has an Apple Mail connection.
https://learn.microsoft.com/en-us/answers/questions/5982193/some-junk-mail-in-outlook-is-flagged

I found a workaround! I had the same issue: Junk emails in Outlook/Hotmail were incorrectly appearing in my iPhone/Apple Mail Flagged mailbox. I checked my Outlook Rules, but there were no rules causing it. What fixed it: I simply renamed the “Junk Email” folder in Outlook Web. After renaming it, the unwanted junk emails disappeared from the Flagged mailbox. Hope this helps others! It was driving me crazy. 😄

I'm sorry... I don't understand. What was the original name of the Hotmail folder you "renamed?" And, what did you rename that folder? Did you do this change on the email folders on the Outlook website... and did not make changes to Apple mailboxes? Thanks for your help.

@Damien said

renamed the “Junk Email” folder in Outlook Web.

I don't understand the "Junk Email" folder can not be renamed in Outlook Web ( https://outlook.cloud.microsoft/ )

@Betty Bauer said

don't understand. What was the original name of the Hotmail folder you "renamed?" And, what did you rename that folder?

I assume this is in reply to the comment by @Damien ?

Yes. I need clarification of the directions of what he did.

@Betty Bauer @Hornblower409

You can try firstly identify where you find these wrong flagged email, the mines are not the the inbox, but in another fold named Junk mail (maybe I created this fold long time ago). I just renamed this fold "Junk mail" to another name. When I come back to my Iphone's mail, "with flag" fold removes all wrong flagged emails.

It's my experience, they are not coming back again until now.

Betty,

It is possible that Apple Mail created the "Junk mail" non-standard folder (vs "Junk Email" Outlook Standard).

Do you also have a "Junk mail" non-standard folder?