Exchange 2010 - no external outlook connections

[effiecgu]

I have an SBS2011 server, with Exch2010
Mail flow is OK
Internal users connect OK
external OWA + mobile phones connect OK.
Lately, without making any config changes, I'm unable to configure any external computer to access externally via Outlook (2013 & 2016).

When running the "new account" wizard, it pops up the window to enter the password again and again, about 10 times, and then just revolves without advancing.

Ideas?

 

[RCHavok797]

Go to the following site and run the Outlook Connectivity and Outlook Autodiscover tests.
https://testconnectivity.microsoft.com/

 

[YeOldeStonecat]

SSL cert and autodiscover correct? Only need port 443 open/forwarded.

 

[effiecgu]

Go to the following site and run the Outlook Connectivity and Outlook Autodiscover tests.
https://testconnectivity.microsoft.com/

Can't use it. sorry.
I tried maybe 100 times, with chrome, firefox & IE, I get "verification failed" each and every time, even on the most obvious characters. something is wrong with that page.

 

[effiecgu]

SSL cert and autodiscover correct? Only need port 443 open/forwarded.

they seem to be OK.
The cert is from a trusted CA, and the date is valid.
I do get a message that the name doesn't match the name of the site (because the server is identifying with its internal name, and the cert is for the external name?) is that critical? If I'm not mistaking, that has been the situation since setup, and we didn't those problems back then.

 

[TurricanII]

Check all the automatic services have started on the server. Sometimes some of the Exchange services do not start after a reboot. Never had a problem with testexchangeconnectivity site myself, try another computer!

Have you rebooted the server yet or at least running IISRESET to restart IIS?

Check the SSL cert, has the date expired? Run the Fix My Network wizard on SBS 2011 to generate a new self signed in-date cert.

Do you have existing Outlook 2013 and 2016 clients still working remotely with no problem?

Is the Outlook Anywhere feature enabled on each mailbox in Exchange 2010?

 

[effiecgu]

Check all the automatic services have started on the server. Sometimes some of the Exchange services do not start after a reboot. Never had a problem with testexchangeconnectivity site myself, try another computer!

Have you rebooted the server yet or at least running IISRESET to restart IIS?

Check the SSL cert, has the date expired? Run the Fix My Network wizard on SBS 2011 to generate a new self signed in-date cert.

Do you have existing Outlook 2013 and 2016 clients still working remotely with no problem?

Is the Outlook Anywhere feature enabled on each mailbox in Exchange 2010?

1. All services are loading OK. Tested the testconnectivity site from 4 different machines (3 locations), all having same error message. attaching screenshot.
2. Server was rebooted several times.
3. SSL was purchased from GoDaddy, is valid until may 2017, it's been working for a few years.
I do get a message that the name doesn't match (internal/external names), but it hasn't been a problem before.
4. I have 2 more Outlook 2016 connecting externally, which were configured months ago, and are not having issues. Only new connections.
5. Outlook anywhere is enabled for all users.

 

[RCHavok797]

Can't use it. sorry.
I tried maybe 100 times, with chrome, firefox & IE, I get "verification failed" each and every time, even on the most obvious characters. something is wrong with that page.

That site always works for me. I just tried it and it will not take the verification code. Thanks Microsoft.

 

[YeOldeStonecat]

I do get a message that the name doesn't match (internal/external names), but it hasn't been a problem before..

Historically we used to do the UCC SSL certs..the 5 name ones...and jam in the internal, external, shortened host name, etc.
Since those stopped being done as a standard, we only do the public/external name now for the SSL cert...and we make Exchange reflect that name. And for internal autodiscover use, you'll need to ensure the firewall is supporting loopback properly.

 

[effiecgu]

Well, just so this thread isn't left open - eventually I disabled Outlook Anywhere altogether, and then re-configured it, and it started working.
Thanks everyone for the responses and the good advice.