Solving IIS SMTP mails stuck in Queue folder when using Gmail

It is actually quite easy to setup a local SMTP and routing through Gmail to test sending emails from your application. There are a few good posts on this that you can follow:

I however had an issue where the mails would get stuck in the Queue folder (e.g. C:\inetpub\mailroot\Queue).

I tried turning off Windows Firewall and enabling POP in Gmail but it did not help.

In the end it was because 2-factor authentication was enabled on my Gmail account. Disabling this fixed the issue for me. Here is a help document for disabling 2-factor authentication, just in case you need it: https://support.google.com/accounts/answer/1064203?hl=en.

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About Bernado

Based in Australia, I am a freelance SharePoint and Dynamics CRM developer. I love developing innovative solutions that address business and everyday problems. Feel free to contact me if you think I can help you with your SharePoint or CRM implementation.
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