Mail is red flagging all sent messages

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Level 1

0 points

Mail is red flagging all sent messages

Hi,

This is my first time posting in the community as I am ALWAYS able to find a fix for any Apple issues by searching the web. However, I am completely stumped on this one.

Since upgrading to Mavericks, every single message I send in Apple Mail on my exchange account gets automatically tagged with a default red flag. No matter what I've done so far, I cannot stop mail from automatically flagging all sent mail.

This does not happen with my 3 Gmail accounts I have running in mail.

Additionally, when the messages are flagged, they are only flagged in Mail. When I look in Outlook 365 online, the messages are not flagged.

I have tried to rebuild mailbox, went into System Preferences and unclicked 'Mail' under my exchange account in Internet Accouts then re-checked it. I have no idea what else to do as I have not been able to find any semi-related topics anywhere like this.

Any suggestions?

Thank you!

MacBook, Mac OS X (10.5.7)

Posted on Dec 4, 2013 6:57 PM

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Answer 1

vicky i

Level 1

9 points

Oct 14, 2017 10:12 PM in response to Linc Davis

I have someone who is using my own e-mail address to send me spam. I can see the actual e-mail address when I click on it. I tried to reply to the address and it was cited as unable to be delivered by my e-mail server. Later I see these same messages delivered into my account. How do I get rid of this?

Thanks,

Vicky

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Answer 2

Tlix

Level 4

1,425 points

Dec 4, 2013 7:27 PM in response to bxl80

Is there a rule in Mail -> Preferences -> Rules that might be flagging them?

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Answer 3

Linc Davis

Level 10

209,547 points

Dec 4, 2013 8:24 PM in response to bxl80

The mail server probably has a web interface. If so, log into it and see whether the messages are flagged there.

Mail rules don't affect outgoing mail. However, if you are automatically CC'ing yourself on outgoing mail, the CC's could be flagged.

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Answer 4

bxl80 Author

Level 1

0 points

Dec 5, 2013 7:02 AM in response to Linc Davis

Thanks for the tips but unfortunately neither work. I have no rules set or created in mail. Also, I've already logged into my exchange webmail (Office 365) and the flags that get auto flagged in mail do not appear to be flagged on the webmail.

Any other tips?

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Answer 5

bxl80 Author

Level 1

0 points

Dec 5, 2013 7:25 AM in response to Linc Davis

Linc - I just re-checked and the messages are now Flagged in the online portal.

Some additional information that I did not think was a factor before is my work issued me a Blackberry about a week ago and this Flag issue started to act up right around then. I have a personal iPhone that never gave me a problem.

I did another search online and it looks like the Blackberry might be the culprit. A combination of Apple Mail, Blackberry and Outlook 365. I've emailed my IT guy at work but any other ideas or help would be greatly appreciated!

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Answer 6

Linc Davis

Level 10

209,547 points

Dec 5, 2013 8:06 AM in response to bxl80

I don't know of any way Mail could be doing what you describe. This sounds like a server issue.

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Answer 7

bxl80 Author

Level 1

0 points

Dec 5, 2013 9:42 AM in response to Linc Davis

I've found a related forum on the Outlook 365 website, no one has an aswer there either.

http://community.office365.com/en-us/forums/158/p/29931/161700.aspx

Looks to be a combination of using Blackberry, Mail and Outlook 365.

Will post any additional findings. Linc, you are right, I am sure it has to do with the compatibility between servers but I dont understand why it would only happen when sending from Apple Mail? I've tested sending messages from the webmail and the blackberry and they do not flag the sent messages.

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Answer 8

Eric Root

Level 10

684,039 points

Dec 5, 2013 11:21 AM in response to bxl80

You might try using another e-mail program to see if the same thing happens.

Mail Alternatives – 9 Free Email Programs

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Mail Alternatives Review (2)

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Answer 9

IrieJ

Level 1

0 points

Feb 12, 2014 3:46 AM in response to Eric Root

Any solution to this ongoing issue with Mail app?

Im experiencing the same problem with the red flag apprearing sporadically on some of my messages. It seems is adding a flag to some of my mails when sending to certain outlook receivers (and not others)?? - Important to note that this happens regardless of whether the priority level is set to low or high.

Thanks for any advice on resolving this frustrating issue.

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Answer 10

Robbeh_1

Level 1

0 points

Mar 31, 2015 12:06 AM in response to bxl80

Hi,

I had this same issue (email I sent from OS X ended up flagged) - I eventually found out what was causing it, altho not how to fix it.

After various tests, the flag appears to be added when a Blackberry handset checks for mail, if you turn off your Blackberry your sent email will no longer have a flag automatically added to it.

The downside to this, is anyone who you are sending email to, who also uses Office 365 and has a blackberry, will get a flag on your email when their blackberry checks for email.

I can only guess its something to do with the mail headers that OS X Mail.app is adding and blackberry are acting upon.

Either way, hope that helps you some.

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