Is calendar synchronization between Office 2013 and Outlook.com capped by spam or bandwidth limits?

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Paul Van Cotthem

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Outlook version
Outlook 2013 32 bit
Email Account
Outlook.com (as MS Exchange)
My set-up:

  • I am using Outlook 2013 (32-bit) on Windows 8.1.
  • I have an Outlook.com account (for mail, contacts and calendar), all of which are synchronized via the Exchange ActiveSync protocol.
  • My Outlook.com calendar is set as the default calendar in Outlook 2013.
  • My Outlook.com data file is set as the default data file in Outlook 2013.

The issue:

  • When I add a single appointment to my calendar in Outlook 2013, it usually at once and correctly with the online calendar on the Outlook.com website.
  • When I add multiple appointments to my calendar in Outlook 2013, and I leave enough time between adding them to the calendar, they usually synchronize at once and correctly with the online calendar on the Outlook.com website.
  • However, when I add multiple appointments to the calendar, in quite rapid succession (i.e. with only some seconds between adding each appointment, for example when adding appointments with a number of my customers for the next day), it often happens that only the first few appointments I added in Outlook 2013 are synchronized correctly to the Outlook.com calendar, but not the remaining ones. These latter ones are indeed added to the Outlook 2013 calendar, but they are NOT synchronized to the Calendar on the Outlook.com website.

Questions:

  • Is this normal behavior?
  • I am suspecting that there is some sort of synchronization issue between Outlook 2013 and Outlook.com via EAS protocol.
  • Could it be that the Outlook.com calendar servers cannot handle synchronizing multiple appointments in rapid succession?
  • Could it be that the EAS protocol cannot handle synchronizing multiple appointments in rapid succession?
  • Could it be that this is some sort of "spam protection" control on the Outlook.com servers: e.g. the connection between the Outlook 2013 client software and the Outlook.com calendar server is cut off when the number of added items during a certain time frame exceeds a certain limit)? I know that there are spam protection limits for mail messages on Outlook.com: one cannot send more than a certain number of messages during a certain time; if one does: sending of mails is halted for a while, messages remain in the Outbox until the "delay period" is over.
 
It's normal behavior, although I'd say it's not the expected behavior. It is a known issue - usually affects people who drag and drop appointments from a pst to the outlook.com calendar. I've never had anyone complain that it happened when they manually created appointments in the calendar, but I'm guessing you do it faster than most people do.

AFAIK, it's not spam protection, just some problem with the server-outlook-eas, I'm not exactly sure which one gets the most blame. It's possible the mail protection is applied to all content, but i thought that was done at the smtp server and the calendar uses the calendar server.

They are rolling out some server updates later in the month, i have no idea what the updates are, but hopefully they fix this and a lot of the other problems.
 
Here is an example of a test I just did, which re-produces the problem:

  1. Open Outlook 2013 application, and open its Calendar window
  2. Open Chrome web browser, go to www.outlook.com, go to its Calendar-window.
  3. In Outlook 2013, put the cursor at the 9:00 am time, type the letter "a" to add a 30-minute appointment.
  4. In Chrome, refresh the web page. Notice that the appointment is indeed there, so synchronization was for the first appointment "a" was fine.
  5. In Outlook 2013, put the cursor at the 9:30 am time, type the letter "b" to add a 30-minute appointment.
  6. In Chrome, refresh the web page. Notice that the appointment is indeed there, so synchronization was for the second appointment "b" was fine.
  7. In Outlook 2013, put the cursor at the 10:00 am time, type the letter "c" to add a 30-minute appointment.
  8. In Chrome, refresh the web page. Notice that the appointment is indeed there, so synchronization was for the third appointment "c" was fine.
  9. In Outlook 2013, put the cursor at the 10:30 am time, type the letter "d" to add a 30-minute appointment.
  10. In Chrome, refresh the web page. Notice that the appointment is indeed there, so synchronization was for the fourth appointment "d" was fine.
  11. In Outlook 2013, put the cursor at the 11:00 am time, type the letter "e" to add a 30-minute appointment.
  12. In Chrome, refresh the web page. Here, I notice that this appointment is NOT visible in the Outlook.com calendar, so synchronization for the fifth appointment "e" did not work.
  13. At the bottom of the Outlook 2013 window, I now see this warning message:
    FileDownloadHandler.ashx

    Note that this "DISCONNECTED"-warning only appears when I add a number of appointments in succession, as outlined above. The EAS-connection does not disconnect by itself in any other circumstances.
  14. So, the first 4 appointments synchronized correctly, but as of the 5th they were no longer synchronized to Outlook.com. From then onward, anything that I add does not synchronize any more. I have to wait for a certain amount of time (I have not been able to determine how long I need to wait), after which synchronization will work again for newly added appointments. However, making changes to the appointments that were NOT synchronized will not work. I will have to delete those and enter them again.

IMPORTANT: in the example, the synchronization failed as of the fifth added appointment. However, this is not always the case, sometimes it happens as soon as after the second addition, sometimes only after ten or more. I cannot predict after how many additions synchronization will fail for a certain duration, after which it will just start working again.

SCREENSHOT 1:
Outlook 2013 calendar shows 5 appointments, "a/b/c/d/e"


FileDownloadHandler.ashx


SCREENSHOT 2:
Outlook.com calendar shows only 4 appointments, "a/b/c/d",
appointment "e" is not synchronized


FileDownloadHandler.ashx
 
I have the exact same problem and would appreciate a fix or workaround
 
I'm stuck in the same agonizing rut.

Posting a few calendar items works fine. But just when you think it will finally work, you post a few more and it stops syncing. Then you're stuck in limbo with some items on one calendar and some on the other. I've cleaned out my live accont online and started with a fresh empty outlook on my pc, but still have the same problem.

My details, Outlook 2013 (32) on my Windows 7 PC, trying to sync my .live account through to my Outlook 2013 (64) on my Windows 8 tablet. Also using the Outlook.com adroid app.

PS Diane, I have always enjoyed your help and posts. Thank you. I'm hopefull for another of your solutions here.
 
Bump.

This is incredibly annoying. I'll not be renewing my 365 subscription if I can't find a fix for this.
 
The only information I have is that they are working on a long list of problems between Outlook.com and Outlook. Make sure you keep Outlook updated - the fixes on the outlook side will be in the monthly releases.
 
Fyi, very same issue here. After an unpredictable number of new appointments, Outlook 2013 x64 on my Win8.1 PC shows something different than Outlook.com calendar on IE11.
Diane, would you know when the expected fixes are supposed to be released? And thanks for your help, much more to the point than official MS postings.
 
No, I don't. I don't have contact with that product team. It looks like calendar categories sync now, so a minor update was rolled out in recent weeks.
 
I also am having sync issues. I use Outlook.com with a POP3 mail account. Everything works well except for reoccurring calendar items. I use Outlook 2013. If a reoccurring meeting is created in Outlook 2013 it seldom syncs to Outlook.com. Standard meetings seem to sync OK, but reoccurring seem to be a problem. Any thoughts?
 
Thanks, I had seen that KB, but did not think it applied to my scenario. Clicked on the copy to my calendar button on the tool bar and it pushed it up to Outlook.com. Now I have duplicates in Outlook 2013, but that is easily fixed. Thanks
again!
 
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