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Has anyone had recent issues with iCloud mail and Outlook 2011?

Two days ago without warning when sending an e-mail from Outlook 2011 from a MacBook Pro running 10.8. (Have a .mac account), I had an error pop up, see below.



"User uploaded file]

Tried entering the password but the same error popped up. Thought there might be an error with the keychain so verified and ran a repair. Still the error continued. I checked that the password was still working and logged into iCloud. I then launched Mac Mail and this worked fine and so also my iPhone / iPad etc. Nothing I did made it possible to send e-maills from my .mac account although I could receive them.


For the last couple of days I have been using my MacBook AIr for sending mails for the same account via Outlook 2011. This has been working fine all day until 25 mins ago when the same error message popped up on this Mac too. Went through the same set of tests and again Mac Mail works and so does the password.


Have tried to Google for a solution but can't find anything relevant. Could this be Microsoft trying to cause problems for Apple users, some rogue update, iCloud security certificate issue, or something more sinister. Any suggestions for a fix gratefully received, as currently I can't use Outlook 2011 on either Mac.

MacBook Pro (13-inch Mid 2009), OS X Mountain Lion (10.8.5), Mid 2009 2.53Ghz Intel Core Duo

Posted on Sep 28, 2013 6:38 AM

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37 replies

Jan 7, 2014 3:50 AM in response to a.winther

I also have intermittent issues with Outlook 2011 / iCloud mail.


1. No matter how often I enter my password, whether in the account information or the "do you want to re-enter your password" pop-up, it will not stick and has to be re-entered each time I open Outlook, sometimes also when Outlook has been open for a while.


2. On some days, mails from the iCloud server are simply not received into Outlook. They show up in the iCloud webmail, my iPhone and my iPad, but not in Outlook. After a restart of Outlook, at some point they might finally show up.


For what it's worth, Csound1 is absolutely right: This is a Microsoft problem, not an iCloud issue. IMO, the only reason MS still supports Outlook for Mac is Exchange, they don't really give it a hoot whether it plays nice with iCloud or not, so it. If you contact MS support, they'll probably just blame it on iCloud, or they will suggest you try this:


1. Delete the iCloud account you have set up in Outlook.

2. Backup and rebuild your database (MS Database Utility). Follow instructions from: http://support.microsoft.com/kb/2360509/en-us

3. After rebuiilding, add the iCloud account and see if that solves the issue. If it doesn't, follow instructions for building a new identity, and add your iCloud account to that.


Provided you enter your information correctly ⚠ this should clear the problem up (at least for a while). If it doesn't, consider an alternative email solution, or just drop the idea of adding your iCloud account to Outlook and instead, sign into your iCloud web interface, go to Settings > Preferences > >General > Forwarding... and set your iCloud mail to forward a copy to an account that works with Outlook. That's what I'm doing!


BR,


OW

Jan 8, 2014 8:10 AM in response to HamburgO

No, that is incorrect.


Dav services will sync with iCal (and not Outlook as you know) and Outlook (prior to Mavericks) will sync with iCal via syncservices, but it syncs to a different account in iCal. Specifically Outlook syncs to the On My Mac account (Calendars and Contacts) and not to the iCloud account.


This remedy fails.

Has anyone had recent issues with iCloud mail and Outlook 2011?

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