Outlook 2010 Won't Send

[tw33k]

Since upgrading, I can't send from my Work account. It just times out. The account is IMAP connected by SSL. No problems when I used 2007 and I just sent from my phone so I know the account is working. Settings haven't changed and are correct. I've tried disabling all add ins.
Any ideas?

 

[Bill2]

Check if antivirus is interfering. Disable antivirus check of outgoing mail.

 

[tw33k]

It's definitely not my AV. It just won't connect to to port 443 (SSL). 2007 worked no problem. Problem only happened since upgrading today.

 

[Bill2]

Try sending with SSL off.

 

[tw33k]

Try sending with SSL off.

Won't work. It will only connect to the server using SSL.

 

[Bill2]

Can you test connectivity to port 443? It may be blocked by a firewall or some network settings.

 

[tw33k]

Can you test connectivity to port 443? It may be blocked by a firewall or some network settings.

It's not. Like I said, all was fine under 2007 and nothing has changed except I now use 2010. The firewall's not blocking anything, the account's working because I can send on my phone. The only change is 2010. I even deleted the account and started again. Same problem. Can receive but not send. It only happens on this account. Gmail and Hotmail accounts work.

 

[Bill2]

Yes, but gmail and hotmail would be using different outgoing ports.

 

[Masan]

Do you have an active VPN connection? This will interfere with your outgoing mail.
It would help if you post the full error you receive.

 

[BrandanL]

Outlook 2010 won't send my email either

I have similar problem. I can recieve email, but not send. I get "421 Cannot Connect to SMT".
Everything was working perfectly until I upgraded to Office 2010 and outlook 2010 from outlook 2003. I was on the phone with my Verizon DSL ISP tech support for an hour attempting to fix it, verifying all settings were correct and trying different port numbers. I reloaded Office and Outlook 2010, moved some mail to a new .PST file, nothing works.