Outlook emails dont work behind ISA 2004
Hi,
I desperately need some help. I set up a network at a client site and i basically got the whole job done and everything was fine except that they cant send or receive email using outlook (email hosted externally).
They've got a normal adsl router that has an ISA 2004 box sitting behind it which acts as an edge device for the network. I set up all the IP's and everything else (but i wouldnt be surprised if i've messed up the IP's which is why i've attached a copy at this link: http://www.thedowra.com/temp/photo.JPG).
Basically, after setting everything up - clients can do their surfing and access FTP etc... but for some reason, they cant send or receive emails through outlook. I did some monitoring to see if any packets are dropping out, but i cant see anything get blocked. I can see the SMTP connections get initiated then closed (gracefully) but nothing is getting blocked and no errors.
I checked my rules and created a rule that allows SMTP, IMAP, POP3, DNS, HTTP/HTTPS from internal to external for all users, but it still would not work. When i got desperate, i created a rule to allow all traffic externally - and that still did not fix the issue.
While doing further testing, I noticed (and i think this is the main issue) that i am unable to telnet to an SMTP server from any of the client machines, but telnet works fine from the ISA box. I guess telnet not working indicates that something is blocking SMTP? Only problem is there are no error reports of ANYTHING being blocked? What is blocking port 25 and how? The moment i take out the edge device (and instead set the modem/router as the gateway) everything works fine, including outlook and telnet etc - so that would rule out the router as the problem?
Im using the Firewall client and have set the disabled flag to '0' for outlook, so that outlook should be working, but still no success.
Does anyone have any insight at all???
I desperately need some help. I set up a network at a client site and i basically got the whole job done and everything was fine except that they cant send or receive email using outlook (email hosted externally).
They've got a normal adsl router that has an ISA 2004 box sitting behind it which acts as an edge device for the network. I set up all the IP's and everything else (but i wouldnt be surprised if i've messed up the IP's which is why i've attached a copy at this link: http://www.thedowra.com/temp/photo.JPG).
Basically, after setting everything up - clients can do their surfing and access FTP etc... but for some reason, they cant send or receive emails through outlook. I did some monitoring to see if any packets are dropping out, but i cant see anything get blocked. I can see the SMTP connections get initiated then closed (gracefully) but nothing is getting blocked and no errors.
I checked my rules and created a rule that allows SMTP, IMAP, POP3, DNS, HTTP/HTTPS from internal to external for all users, but it still would not work. When i got desperate, i created a rule to allow all traffic externally - and that still did not fix the issue.
While doing further testing, I noticed (and i think this is the main issue) that i am unable to telnet to an SMTP server from any of the client machines, but telnet works fine from the ISA box. I guess telnet not working indicates that something is blocking SMTP? Only problem is there are no error reports of ANYTHING being blocked? What is blocking port 25 and how? The moment i take out the edge device (and instead set the modem/router as the gateway) everything works fine, including outlook and telnet etc - so that would rule out the router as the problem?
Im using the Firewall client and have set the disabled flag to '0' for outlook, so that outlook should be working, but still no success.
Does anyone have any insight at all???
Comments
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Khattab Member Posts: 97 ■■□□□□□□□□a number of views so far, but no responses..... has no one seen this before??
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Claymoore Member Posts: 1,637Outlook will connect to internal servers (which it believes these are) using secure smtp over port 587, so check that port.
Exchange Network Port Reference: Exchange 2010 SP1 Help
You should also check the Exchange connectivity status and test autoconfiguration by using Ctrl+Right-Click on the Outlook icon in the system tray for any errors. -
Daniel333 Member Posts: 2,077 ■■■■■■□□□□Not an ISA genius, still learning...
Permit incoming from the IP range of the hosted Exchange provider?
Ensure you are allowing encrypted traffic in/out?
Use route print to ensure you have correct routing?
Make sure your DSL modem is in bridging mode?-Daniel