Problem with ASA 5505 and external exchange server

primusoffice — Mon, 11 Mar 2019 20:20:12 GMT

Hi,

we are useing a ASA 5505 and connect to an external Exchange Server (Microsoft Online Services) via Exchange Proxy over https.

Everything is going well, after some time Outlook (2003) is not able to send Emails any more. (Could not establish connection to Exchange Server)

After restarting the Server (we are working in Remote Desktop) everything is ok again for some hours or so.

Before we used a PIX 501 and had no problems.

I would be thankful for any ideas, what could be the reason....

Re: Problem with ASA 5505 and external exchange server

Shrikant Sundaresh — Wed, 13 Apr 2011 13:45:45 GMT

Hi Walter,

You could check a few things to see what's going wrong:

1. When outlook cannot send mails, can you ping the exchange server?

If you can't ping, then do a packet-tracer command on the ASA to determine if and why the ping packet is being dropped.

packet-tracer input tcp detailed

If the packet is dropped on the ASA, this command will tell you why.

2. Are there any connection limits configured for the exchange server. These can be configured in either the policy-map or in the static nat commands.

3. The 5505 base license has a limit on number of internal users. So if this outlook problem is only for a few users, and ASA has base license, then it could be because of limited users.

4. You can run captures on the ASA on both interfaces, to see packets to-and-from the Exchange server. If you see packet entering the ASA and leaving, but no reply coming, then it could be an issue with the server.

Hope this helps.

-Shrikant

topic Problem with ASA 5505 and external exchange server in Network Security

Problem with ASA 5505 and external exchange server

Re: Problem with ASA 5505 and external exchange server