I'm running into this issue right now, some servers i send e-mail to are fines, and some servers stay in Exchange with the error: Remote server did not respond to a connection attempt. I nslookup them and it resolves, so it isnt a DNS issue, where should i start to troubleshoot these ?
There are no events in the event viewer regarding this. However a user told me he had to auth to a smtp server to try sending e-mail, which is weird cause he's going through exchange. Here's what i got from dnsstuff;
PTR MISSING! 67.69.108.122 has no reverse DNS entry; some mail servers may not accept your mail. 1200 seconds 0 ms
1. There was a SMTP communication problem with the recipient's email server. 2. You do not have permission to send to this recipient.
I guess this is all related to my problem, I was also reading stuff about it. It could be related to a DNS issue, where the remote mail server couldn't be able to reverse lookup of the mail server and take it as spam e-mail.
Yea, i solved it, i'm now using the ISP smtp server in exchange and everything works fine, i asked the ISP to add a PTR for our server, which will be done shortly, and hopefully solve the issue.