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Last week we've transitioned from our POP3 email provider to Office 365 for Business. We have 30 users and started a mailbox copying and synchronization batch job on their new mailboxes. As of today there are only 4 mailboxes left which are still synchronizing. We have a very slow (1 mbit) upload bandwidth so we did expect a long completion time.

Our problem is that some of our users whose synchronization jobs have already finished do experience some strange behaviour with email delivery.

One of them did try to check his inbox on the weekend at home. He couldn't see his daily email traffic in his inbox and so checked his OWA account to confirm it. His OWA inbox was empty, too, so he assumed that it was the real thing. After turning on his laptop and firing up his desktop Outlook application he could see a big amount of emails in the inbox. After opening the desktop app his phone did begin to get those emails, too, and when he went to his OWA account he saw them in there, too.

Another user did send some emails from his Gmail account to his Office365 account and checked his phone app to control the inbox. He didn't get the emails. He went to his OWA account to check them and those emails were in there. After awhile when he opened his desktop Outlook app his phone started to get those emails. He went through this process a couple of times.

Those problems haven't been reported to me by all our users. Only a few of them did experience them.

It seems like that the desktop Outlook app is somehow triggering the mail flow.

We have some other minor glitches but our main focus is with these problems right now. I couldn't find any exact or similar reported problems on MS forums or here. Our channel partner only responds with classic answers which mainly focus on the unfinished company wide Office365 synchronization issue. I don't believe them because one of our users did experience this problem on his home connection and that user's synchronization was finished.

Did anyone else have had these problems, and if so how did you solve them?

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The only thing I can think off is that perhaps MX records/auto-discover settings aren't configured properly.

If possible, please can you provide me with your domain name? I would suggest you make sure the following is complete.

MX Records

  • Turn off send/receive connectors for your old online exchange (if possible).
  • Within the DNS configuration for your domain, make sure you have a) setup the Office 365 MX records and that b) they're a higher priority than the old ones. (Delete the old ones if you're no longer using the old exchange).
  • The above change can take up to 72 hours (rarely), but in my experience takes about 15-30 minutes to propagate.
  • Clear the DNS cache on the devices in question, - remove/re-add mailboxes to make sure that the device is using the most up to date MX records and that they're connected to O365 properly.

Auto-Discover/ActiveSync

Most mobile devices will use auto-discover to connect to O365 and ActiveSync to push emails from the O365 server to the device. Please make sure you have completely the following:

  • Make sure your DNS CNAME records for auto-discover point too: autodiscover.outlook.com
  • Use the RCA (remote connectivity analyzer) tool to check your domains auto-discover configuration, - this will report any errors.
  • Again remove and re-add email accounts on the mobile devices.

Please also read through this Microsoft KB to set up and manage domains in Office 365.

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  • I'll accept your answer because it includes the most detailed control steps. But our problem wasn't solved with them. We opened some tickets to MS support but they didn't solve them, too. These problems were gone after a few days without anyone interfering. We are still observing our mail flow.
    – Montag451
    Jul 23, 2014 at 6:07
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Keep in mind that folder in an MS-Exchange environment are synched folders.

If you move a single message to the folder in outlook, the synch to the server folder happens very quickly and on the spot. Thus making it available to be synched by other devices.

On the other hand you have done many 1000's of messages at once, multiply that by 30 clients all using a single 1mb upload pipe.

OWA is nothing more the a client running in a browser, it's not really anymore of a 'direct look' at the mailbox than any other client is.

In short, what is happening is synchronization of the synched folder on the work desktop has stopped because of excessive network traffic. Accessing the folder is causing it to begin the synch process again.

Eventually this should work itself out. On the send/receive tab in Outlook 2013 there are folder update buttons that may be used to help the process finish.

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  • I'm aware of the synchronization process and I know what OWA is. If you would read my post carefully you can find out that I know this and already mentioned it in there. These users who had problems were the ones whose syncs were finished.
    – Montag451
    Jul 21, 2014 at 11:11
  • I did carefully read your post, I've also "been there, done that". You say the users synch was finished, but I'm not sure you understand WHICH synch was finished. You have synched many messages to a users local Outlook, but those local copies haven't synched to the server folder, this when someone logs in from another source the server is unable to provide the information it doesn't yet have.
    – Tyson
    Jul 21, 2014 at 14:04
  • The sync to the server folder for these users was finished after about 1-2 days of folder upload to the server and after it Outlook did show the message "All the folders are up to date". Up to that point Outlook was always showing the message "Synching xxx folder" etc. This message did not show until all the folders were uploaded and it took different time lengths for different folder sizes of different users. Local copy doesn't take hours, it takes minutes. For example a heavy loaded folder's local copy can take up to 10-15-20 maybe 30 minutes whereas light folders do take only a few minutes.
    – Montag451
    Jul 21, 2014 at 14:13
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Personally, I would say to disable the exchange cache mode. This will stop sync of the mailboxes, and only show an online copy.

We've had to do the same for clients with bad connections.

In Outlook 2013: "File" > "Account Settings" > Choose which mailbox, and click "Change", disable "Use cache exchange mode".

We have been transferring some of our clients to Office 365, all have had teething problems.

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  • First of all we don't trust Microsoft so much. You can call us paranoid but almost 10 years ago our nationwide ISP was hit by an undersea fiber cable accident and we had to sip the internet nationwide for a few days. So we need the local mailbox cache. The second problem is that if we use the online mode that would burden our bandwidth too much. We don't have much spare bandwidth.
    – Montag451
    Jul 21, 2014 at 11:19

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