Emails Wont Upload to from MS Outlook 2010 to Server

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I've been attempting to resolve this issue myself for a month and would really appreciate some help. Here we go:

I have dozens of embedded folders full of mail that I copied to my account on Outlook 2010. I had expected these to upload to so that I could access them anywhere. Instead, only the file folders uploaded.

Software: Outlook 2010 x32 (on W8.1) with Hotmail Connector
Email account: and


MS Outlook 2010 and are communicating insofar as test emails sent from each source show up in the other's inbox, but the send folders aren't syncing and my named file folders remain empty on the server.

I have uninstalled/reinstalled my account from Outlook 2010 several times, and have done the same with the Hotmail connector. None of my file folders' names exceed 30 characters.

I added an account to Outlook 2010 and attempted to upload a folder to the server and it also failed.

What can I do?
Thank you so much for your reply!

There are many thousands of emails; about 50 folders, and a total pst size of 4.5 GB. The emails are from a pop3 account that was converted to IMAP.

My understanding was that did not support IMAP, only MAPI. Am I wrong? If so, what are's IMAP settings for Outlook 2010? If I am successful with using IMAP, would I one day be able to download my actual emails via the MS Outlook desktop client and import them into another email account like gmail or yahoo?

I should also mention that I did create a new Outlook 2010 profile, which did not solve the issue. The emails that I am trying to upload are now in the form of an Outlook 2010 data file.

Apparently, the information I read about offering only MAPI was outdated. I wish every blogger would date his/her articles! ;-| Please let me know if the following settings I found are correct.

Also, I'd appreciate it if you'd address the remaining question above about my future ability to import/export emails from/to a hypothetical new account.

Incoming IMAP
  • Server port: 993
  • Encryption: SSL
Outgoing SMTP
  • Server port: 587
  • Encryption: TLS
Thanks :)
I am having a similar problem, I think, where my folders from a PST file are not syncing, and Outlook 2010 (same config as original post) eventually becomes unresponsive. When I setup my sync account specifying the Hotmail Connector, it does not give me any options to provide any other protocol. Where were you able to adjust the protocol and settings?
My message edit time has expired -- I wanted to add that in my case, about 60-70% of the emails are being synced. I think it's less than 1Gb, my PST file is 2.5Gb but I'm not moving over everything at once.
Like Jonathan, I'm not moving everything at once. In fact, despite having plenty of system resources available, Outlook 2010 only seems capable of moving data a single file at a time, otherwise it hangs and crashes. Would anyone have step-by-step instructions on how to set up IMAP with the hotmail connecter?
Try using imap - that has always worked here. It should work with the outlook connector too. How much mail is in the folders?

Hi Diane,
I just got installed successfully on MS Outlook 2010 as an IMAP account. I set it up manually with the settings I indicated upthread. However, I did not select the hotmail connecter. How to I get my calender and contacts to sync between the server and MS Outlook 2010 with an IMAP?
Thanks very much!
min, I was thinking of doing what you said, registering as a regular IMAP account and simply removing the hotmail connector. I am wondering then what the Hotmail connector would be for then?
Did you ever get your your IMAP emails to sync? I'm still struggling with it. in particular, I need to know ho wto sync my calendar/contacts if I set up my account as an IMAP account.
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