Outlook 2010 Outbox Message Stuck

[donte10]

I have a company that is using Office 365 and Outlook 2010. This is only a company with 3 users and all are having the same problems, internally at the the office and away from the office. Users attempt to send a few messages (no attachments) and notices after a few minutes that the messages are sitting in their Outbox folder. If user attempts any of the following to resolve the issue, Outlook will lock up and the Outlook.exe process will need to killed through Task Manager. Even when just sending 1 message the status will be stuck on 'sending 1 message of 1. Updating Inbox.' and never sends. The only resolution is to restart the Outlook 2010 client. Once Outlook has restarted, the message sends immediately. Another test message right away and it works. If trying to send another message after 5 minutes has passed, the problem reoccurs. This occurs frequently 14-20 times a day.

1. Messages stuck in Outbox -> Change Outlook to Work Offline -> Move e-mails to Drafts folder from Outbox -> Change Outlook to Work Online -> Attempt to send a new message -> Outlook locks up

2. Messages stuck in Outbox -> Attempt send/receive process -> Outlook locks up

3. Messages stuck in Outbox -> Attempt to view messages in Outbox -> Outlook locks up

4. Messages stuck in Outbox -> Attempt to delete messages in Outbox -> Outlook locks up

Resolution Steps already attempted

1. Recreated user's Outlook profile from scratch -> Issue persists

2. Removed All Add-ins -> Issue persists

3. Uninstalled Antivirus seucrity software -> Issue persists

4. Started Outlook in Safe Mode -> Issue persists

5. Removed Office 2010 installation and installed a fresh copy -> Issue persists

Not sure if anyone can shed some light on this issue and offer their insight, but any assistance with this issue would be appreciated. I have been working with Microsoft with no luck.

 

[OfficeTechs]

sounds like connectivity issues to me, almost like a connection is dropped when no traffic is detected or possibly even DNS issues although not convinced. Have you tried initiating an SMTP connection via telnet to the office365 mail host? With your office365 you should also have web access via browser (used to be OWA with Exchange), im assuming you have no issues with that?

 

[andcorptech]

EDIT: Sorry didnt read post properly first time. You already covered AV.

 

[KH58]

OP...can you post system info? Recent changes? Is Outook live syncing with some sort of Cloud backup? Was there a recent change in ISP? Where is outlook forwarding mail to ( I.E. for me, Bellsouth changed mail server addresses a few months ago with no real notice sent to me. I had to reconfigure the send/receive mail servers in a couple of mail apps for reliable results.) Is there any error reported in event log? Etc...

 

[donte10]

With your office365 you should also have web access via browser (used to be OWA with Exchange), im assuming you have no issues with that?

I have not looked into DNS issues; nothing has changed on the ISP side of things. Accessing the client's Webmail works fine using the web version of Outlook. I have not tried initiating an SMTP connection via telnet and haven't done this before. How?

The Internet connection doesn't seem to drop; for the client can access the Internet pages when this occurs.

 

[drjones]

Are they using 32 or 64-bit version of Office 2010?

I've read of problems with x64 Office 2010...

 

[donte10]

Client is using a 32-bit version of Office 2010.

Added info: I recently uninstalled 2010 and upgrade to the latest 2013 and the client has the same problem. I had Microsoft on the phone with me today, and they can't find a fix yet either. He is troubleshooting with me. No success, so far.

I have just setup the account on a bench computer to see if the problem is replicated here. I'll let you know if I have the same problem here.

 

[KH58]

I asked about this but am sure if your addressed it. Is the mail live syncing with some sort of Cloud storage/mail service, etc? If so try disabling that function and test.

 

[drjones]

Have you tried setting up outlook on a fresh, spare machine you've got & seeing if the problem manifests?

Have you tried creating an entirely new Windows profile on one of the current machines & seeing if that helps?

Is there any pattern to whom these emails are being sent? Is it autocomplete or a freshly typed in address? Believe it or not, I've seen some funkiness with autocomplete addresses - sometimes you have to delete it & manually re-enter the email address....

 

[Jonathan.iv]

Have you tried to run Scanpst.exe

Hello Donte10
Have you tried to run Scanpst.exe

Scanpst.exe

just google : "How to use the Inbox Repair tool to recover email messages in Outlook"

and you can get the link
Kind regards!

 

[drjones]

Hello Donte10
Have you tried to run Scanpst.exe

Scanpst.exe

just google : "How to use the Inbox Repair tool to recover email messages in Outlook"

and you can get the link
Kind regards!

This is Office 365 - exchange, so there aren't any PSTs, unless there are archives. I believe there is a scanOST tool, but might be easier to just clear the offline cache and force it to re-download from server.

 

[donte10]

Problem turned out to be a faulty router within the Clients office. Replaced it and all worked well again.

 

[drjones]

Problem turned out to be a faulty router within the Clients office. Replaced it and all worked well again.

Can't say I ever would have thought to check that, but that makes perfect sense....if outlook doesn't have a perfect connection, it will freak out like that.

How did you ever discover it was the router??