I'm in a bit of a pickle here. We've recently switched broadband providers and for some reason, our outgoing emails get stuck in the Outgoing folder in Outlook 2010. They only get sent after restarting the application.

I have recently took off DNS and DHCP duties off the router and put them on our W2k8 server, thinking it could help.

Our current accounts are with CobWeb (hosted Exchange), but I have added an Office 365 Exchange account to my profile and that one works just fine. I have done a trace route to CobWeb's Exchange server and I don't see anything strange. This only happens when we are connected over Ethernet, if I connect over wireless directly to the BT Internet gateway, it works just fine.

The connection goes like this:

BT Gateway -> Cisco router (for backup line) -> Switch -> Server and PC's

I have checked every point of failure I can think of, enabled logging in Outlook but couldn't see anything wrong.

What do you think it is?

If you need more details please let me know!

UPDATE: I have ran more tests and the Office 365 account fails too. I am able to send about 3 or 4 emails after opening Outlook, then they get stuck again in the Outbox until the application is restarted.

  • Might be a client-side problem; have you tried the steps you find on Google to deal with emails getting stuck in Outlook's outbox? – HopelessN00b Jan 14 '13 at 21:19
  • Yes, and it's not just me, it's everyone that's using the Ethernet. Also OWA works fine and Outlook outside the office is fine too (home laptop). It's only affecting the Cobweb account, O365 is fine and I renamed, recreated and moved the profile, created a new one, nothing helped. I also tried using plain text and rich text without signatures because of something I saw in the logs, but that didn't help either. – TuxMeister Jan 14 '13 at 21:22
  • I cleared the DNS server's cache, did a flushdns on the local machine, renewed the IP lease, still nothing. Also tried bypassing the local DNS by using Google's, same result. – TuxMeister Jan 14 '13 at 21:23
  • Can you try using a different client (such as Thunderbird) to figure out if it's an Outlook-specific issue or not? – HopelessN00b Jan 14 '13 at 21:24
  • Affecting all users at once? Is that possible? – TuxMeister Jan 14 '13 at 21:26

There was a problem with the Cisco router, it needed to be upgraded. We haven't switched that kit off for more than a year, so when we switched offices it had to be shut down. Once the upgrade was done and the config loaded back in, emails started flowing correctly.

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