New SBS 2003 R2 SP2, w/ Exch 2003 installation (SP2). All mail gets routed and queued correctly except to Hotmail. Mail to any Hotmail account usually sits in the SmallBusiness SMTP Connector Hotmail queue as “Queued” with “0” retries for anywhere from 40 minutes to 12 hours. Other items queue up behind it and then all send successfully at random intervals and are sent successfully.
Also, the queue icon is a plain folder with no “circle” indicating a status (such as check mark or arrow)
Maximum logging and wireshark sniffing show no attempt to contact Hotmail when the item is queued. It just sits there.
- Installed and run the Exchange BP Analyzer (no issues found)
- Manually connected to Hotmail SMTP via telnet with no issues
- Verified DNS and SMTP through the firewall successfully
- Run DNSStuff reports against the domain (reverse DNS issue identified and resolved 5 days ago)
The only thing that tools show as an issue is a blacklisting with Backscatter (but NDR reports have been turned off). If this were an issue though, wouldn’t I see retries and failures?
AV/Anti-Spam is Symantec Information Mail Security