Outlook anywhere issues

[Digital-Vortex]

Hey Guys (and girls? (Thats another topic! ))

Anyway, Looking for some ideas. I have a SBS 2008 server that was recently setup doing a migration from SBS 2008. Some software issues forced the migration but overall it went well.

Anyway, remote users cant access emails over HTTP. I don't want to start doing VPN's due to bandwidth and would rather sort the issues. The server works fine internally but computers that were joined to the domain before the migration just don't connect. trying my own computer thats not on the domain and same results. we are using the SBS self signed cert. Outlook just says it cant connect. DNS works as we can access RWW from the net.

Im wondering if i need to remove the laptops from the domain and rejoin them and its an SSL trust issue, but I am struggling to find anything on this since it is self signed. Any ideas on things to try or look for?

Also, can someone suggest the benefits of getting an SSL cert rather than self signed?

G

 

[zEp]

Hey Guys (and girls? (Thats another topic! ))

Anyway, Looking for some ideas. I have a SBS 2008 server that was recently setup doing a migration from SBS 2008. Some software issues forced the migration but overall it went well.

Anyway, remote users cant access emails over HTTP. I don't want to start doing VPN's due to bandwidth and would rather sort the issues. The server works fine internally but computers that were joined to the domain before the migration just don't connect. trying my own computer thats not on the domain and same results. we are using the SBS self signed cert. Outlook just says it cant connect. DNS works as we can access RWW from the net.

Im wondering if i need to remove the laptops from the domain and rejoin them and its an SSL trust issue, but I am struggling to find anything on this since it is self signed. Any ideas on things to try or look for?

Also, can someone suggest the benefits of getting an SSL cert rather than self signed?

G

Do you know if the "Enable Outlook Anywhere Wizard" was run as that makes all the necessary changes. I think the wizard might want/require a valid UCC SSL cert but not sure and for more reasons than are worth getting into I feel it is better to spend the $100 dollars on a proper cert then hack the system to work without one and pray it never breaks. Mainly becuase all the diagnostic steps and BPA's assume you have it setup properly.

Also look at www.testexchangeconnectivity.com so you can get an inital idea on what is wrong with remote users.

 

[Digital-Vortex]

The site wont progress because it cant trust the cert in the OA tests. All the others you can ignore. Also I cant seem to find the "enable outlook anywhere wizard", but all the ones in the SBS console have been run and ticked.

As for hacking it to work. I have done a few SBS 08 install and so far have never bought the SSL with no issues or hacks required. Granted I get the old warnings in IE for RWW and phones on setup but thats the only thing i have seen. Never been a problem otherwise.

G

 

[KapsZ28]

The site wont progress because it cant trust the cert in the OA tests. All the others you can ignore. Also I cant seem to find the "enable outlook anywhere wizard", but all the ones in the SBS console have been run and ticked.

As for hacking it to work. I have done a few SBS 08 install and so far have never bought the SSL with no issues or hacks required. Granted I get the old warnings in IE for RWW and phones on setup but thats the only thing i have seen. Never been a problem otherwise.

G

Certs are cheap. There really isn't any reason not to buy one.

Can you get to OWA internally? https://server/owa

Did you try "Fix My Network" to see if there are DNS or other issues?

Checked the log files?

Also, why would you have issues with computers not connected to the domain? Any PC should be able to access OWA by going to the URL.

 

[Digital-Vortex]

It's now OWA, that's fine for everyone.
It's outlook anywhere thatsbthe problem. So the PC can use outlook wherever they be.

G