Eric Miller5
Level 1 (20 points)

Q: Keychain problems and Microsoft Outlook Password Prompts Constantly

I manage multiple Macs and have found an error that I am unable to fix. Outlook is constantly asking for the passwords for these specific accounts. There is no ryhme or reason the behavior.

 

- The Macs are running 10.9.1

- Microsoft Outlook for Mac is version 14.3.9

- The problem email accounts are connecting to a mail server running Communigate ( not sure the exact version, but its likely 4 years old )

- Running Verify Keychain will sometimes show that the keychain needs to be repaired and will show the mail accounts Item “mail.xxxxx.com” has unspecified value for port attribute. It happens on the imap item and the smtp item. The smtp port is non standard at 1200.

- There are 5 mail accounts in total on the worst offender, 3 that connect to the Communigate server and 2 that are Exchange.

- The Exchange accounts will sometimes ask for password, but never show the port error in keychain repair.

- I have reset the keychain multiple times, made sure its the default and made sure it is not locked.

- This was happening in 10.8.5 as well, so I don't think its iCloud Keychain related.

 

I just also added a different users account that uses the same Communigate server to another MacBook Pro and it shows the same behavior.

 

I don't think its the Communigate server, if that wasn't working it would not work all the time.

 

I do believe it is something to do with how the passwords are stored in the Keychain.

 

Anyone else having these problems?

Posted on Dec 22, 2013 10:00 AM

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Eric Miller5

Q: Keychain problems and Microsoft Outlook Password Prompts Constantly

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  • Helpful answers

  • by Marvin Price1,Helpful

    Marvin Price1 Marvin Price1 Jan 14, 2014 9:09 AM in response to Eric Miller5
    Level 1 (19 points)
    Mac OS X
    Jan 14, 2014 9:09 AM in response to Eric Miller5

    Eric,

     

    I am experiencing the same exact problem but my mail server is Kerio Connect. It's happening for one user on one Mac on 10.9.1.  2 Accounts.

     

    Periodically Outlook just requires you to authenticate. It's annoying the crap out of the user.

     

    I've been through quite a littany of possible fixes.

     

    Today I've just wiped her Keychain and created it brand new, providing new passwords for the Outlook email accounts. In both cases the new Keychain entries had the "unspecified value for port attribute" error. I repaired the keychain but I'm not sure it will work. In my case I'm using a fairly standard port... 587 for smtp.

     

    Over on Microsoft's support boards many people seem to be having a similar problem for numerous reasons.

     

    No definite fix is available as of yet, near as I can tell.

  • by Eric Miller5,

    Eric Miller5 Eric Miller5 Jan 14, 2014 5:37 PM in response to Marvin Price1
    Level 1 (20 points)
    Jan 14, 2014 5:37 PM in response to Marvin Price1

    I can't say that I am happy that its happening to you, but glad I am not alone in this.

     

    My next step is to run a packet capture on the device as its making connections, but the problem is that it doesn't happen with any consistency, but does happen enough to have this user considering going back to Windows...

     

    I am hoping that Apple is aware of the situation or that we can get enough traction to make this appear on the radar.

  • by AlexandrianZorik,

    AlexandrianZorik AlexandrianZorik Mar 6, 2014 1:53 AM in response to Eric Miller5
    Level 1 (0 points)
    Mar 6, 2014 1:53 AM in response to Eric Miller5

    I have the same issue, Outlook 2011 + 14.3.9 + Mavericks 10.9.2 + Office365 Midsize bussines asking continiously for credentials not for pop or imap acounts that they were created and saved before upgrade but for new accounts that i have configured now i have tried the steps as Marvin Price1 now its a little bit better because as long as i am not going restart / Close re open the outook again its working but as sonn as i reopen the outlook its asking for exchange credentials and show me the error massage that there is something wrong with your credentials although its 100% correct. its for me looks like keychain probkem but i have tried all keychains options repair create new remove etc... not helped. it would be great to have a soloution soon.

    best regards

  • by Eric Miller3,

    Eric Miller3 Eric Miller3 Mar 6, 2014 7:20 AM in response to AlexandrianZorik
    Level 1 (25 points)
    Mar 6, 2014 7:20 AM in response to AlexandrianZorik

    You need to click on the Outlook application in Finder, Get Info ( Command + i ) and then disable App Nap.

  • by Eric Root,

    Eric Root Eric Root Mar 6, 2014 12:39 PM in response to Eric Miller5
    Level 9 (74,243 points)
    iTunes
    Mar 6, 2014 12:39 PM in response to Eric Miller5

    Apple doesn’t routinely monitor the discussions.

     

    Send Apple feedback. They won't answer, but at least will know there is a problem. If enough people send feedback, it may get the problem solved sooner.

     

    Feedback

     

    Something to check.

     

    Password – Mail keeps asking for Password

     

    Try running Keychain First Aid and resetting the original keychain.

     

    Keychain Reset