Hi All. I have a issue that i am at a loss as how to slove it. I have an ASA 5505 as my firewall. I have users from other companies who visit from time to time and are unable to use their outlook email to send messages. They can however receive messages without a problem. I also have a situation where users who use windows live to access gmail are unable to send messages.
I have narrowed it down to the fact that these uses are using ssl/tls to send the mails. I did some reseach and found out about the inspect esmtp setting in the ASA. I have disabled it and i still have to problem. I have also removed all outbound deny statements and still no luck.
Of note is that i can send emails without atachments. They take a long time to go out ( from minutes to hours) but eventually they do. Emails with attachments of even 10k do not go at all.
I was running image 8.2.3 and i downgraded to 8.0.5...still did not work...i upgraded to 8.4.3...still did not work. I am now back at 8.2.3. I would really appreciate some insite into solving this problem.
My Firewall config is atached. I am at my witts end as to what elese to try. The company has not renewed support for the device so i am on my own here! I would really appreciate you help.
Do you see any syslogs in ASDM for this traffic when a connection fails? That will give us more information about why this is failing.