IIS failure to send SMTP via Gmail

[googlemad]

For many, many years now our Personnel server has been using SMTP in IIS via smtp.gmail.com to send out alerts to staff regarding holidays and the like. Recently it has stopped working with the following message :

 

Message delivery to the host '74.125.136.108' failed while delivering to the remote domain 'ourdomain.ac.uk' for the following reason: An SSL error occurred.

 

Is this Google's way of saying they no longer want anything to do with Windows Server 2003? We would have upgraded except we're getting a new Personnel system soon so no point!

[IrritableTech]

smtp.gmail.com is SSL/TLS only I think are you using that? This page suggests if that's a problem you can use the smtp relay on port 25...

 

https://support.google.com/a/answer/176600?hl=en

[Davit2005]

I recently set up a PostFix server at home and had a bit of trouble which was caused by them blocking less secure mail apps by default.

 

https://support.google.com/accounts/answer/6010255?hl=en

[Steve21]

Although not for GMail what we did for some of our old apps for 365 was setup a local SMTP relay for these (e.g. old photocopiers etc), and then have them point to the relay, and the relay connect to 365 via SSL/TLS

 

Steve

[mweaver]

I am having this same problem (Windows Server 2003, IIS7). The problem started Nov. 20, 2015. I haven't been able to find any news of a change by Google. Have you found a solution or workaround?

 

Thanks!

[googlemad]

Still not found a resolution, got to be something to do with Server 2003 as using the exact same settings on a 2008 / 2012 server it works fine!

[Steve21]

Did it break on the 28th by any chance?

 

Steve

[Steve21]

Reason I ask is they recently changed a lot to requiring TLS v1.2 (as well as pushing SHA256) which isn't support on sub-2008R2 unless they patched it

 

https://www.howsmyssl.com/

 

Steve

[googlemad]

Think it must be to do with that. In the end I've just set up a temporary IIS SMTP server on a 2012 R2 server and relaying through that instead which works fine.

[Steve21]

Think it must be to do with that. In the end I've just set up a temporary IIS SMTP server on a 2012 R2 server and relaying through that instead which works fine.

 

Aye easiest way if I'm honest, got the same for some old photocopiers etc until they're removed/upgraded Also means that the emails save locally if you're internet down and resend once it's up which is nice!

 

Steve