Here is the simple breakdown:
1. Boot Mac from a powered off state.
2. Launch Outlook
3. Observe that Outlook connects and syncs
4. Put Mac to sleep
5. Wake Mac
6. Observe that Outlook is in "Not Connected" state

7. Select menu option Tools > Send & Receive > Send & Receive All

8. Observe that Outlook is in "Not Connected" state

9. Close and relaunch Outlook

10. Observe that Outlook connects and syncs

This happens to everyone I know, not just at my company. Hundreds of man-hours are wasted on this. Lots of embarrassment comes in the form of, "I'm sorry I didn't get it, I didn't notice that Outlook needed to be restarted."

I've been experiencing a very frustrating crash issue with Outlook 2011 over the past few weeks. Essentially, whenever I'm creating or replying to an e-mail and I hover over a contact in the To: or cc: fields, Outlook will crash. 

I've tried to re-build my database but the problem does not go away. Through some trial and error, I think I've narrowed the problem down to the contacts as I created a new identity with just my contacts and I get the same crash problem. 

However, what I'm now stuck on is how to remove this issue from my main identity. I have attempted to simply delete my contacts but this has no impact. 

Has anybody else experienced a similar issue and if so, did you manage to resolve the issue?

Thanks

The Macbook previously had Office 2011 installed on it with all updates. I purchased Office 365 Personal so I would be able to install Office on the iPad and share my Outlook Calendar and Contact data. I was planning to install OWA onto the iPad and thereby keep my contacts and calendar in sync.

I successfully added the account information to Outlook 2011 as directed. However, a yellow dot remains beside the account in the Outlook preferences, indicating it is not connecting. Therefore the information in Outlook is not being uploaded. I have tried adjusting settings to no avail.

I did some research and found one article that suggested this wouldn't work with Outlook 2011 and another suggesting an additional purchase was needed. If so that was not made very clear. Can anyone assist?

Outlook for Mac 2011 14.4.1 (140326)

Connected to Office 365 hosted exchange server.

Each time I attempt to "Open Calendar" for Shared calendars, Outlook is triggering an auto discovery event. In the Outlook log file I see 

 

Outlook Exchange Auto Configure Error code: -3259

What does this error code mean?

I have been struggling with this issue for some time.

As I am typing an email in Outlook (HTML on) the fonts will change mid-sentence sometimes. Sometimes it is just the font size, sometimes it is a completely different typeface.

I do not have any font management application running (i.e., Suitcase) so I don't know what would be affecting this. I also trying clearing out and pref files to no avail.

Thanks.

OS Mavericks 10.9.2

Outlook 14.4.1

MacBook Pro 15 2.6 GHz Core i7

I have synced two accounts to Outlook 2011 (one which is a Microsoft 365 and the other is a BT Yahoo account). The folders from the Microsoft 365 account have synced correctly with Outlook however the folders for the BT Yahoo account have not synced at all. I wondered if anyone else has had this problem and/or had a solution.

Many thanks.

I have decided to make a move to Outlook in the hope it was better than Mail for Mac but it was only once installed I find out that

- there is no way to add an email alias and choose which is the default address the email will be sent

- I can't add schedule to my IMAP folder to stop some account send and receive (just the default one can be selected)

- Outlook doesn't support Caldav and I can't get my appointments shown

- Similarly to the above, I can't enjoy my contacts in the list

I hope to be wrong, but I have spent nearly three hours to read threads everywhere attempting several tricks

Hopefully I'm wrong