I have 2 accounts for different businesses with different email accounts on different servers and both are now presenting this identical problem:
It looks like there was a problem reaching your SMTP service
Error Message: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.0 Authentication Required. For more information, go to
When I click the Routine Emails tab and then go back to SMTP Settings it says:
An activation code has been sent to you using your SMTP mail server settings.
Please enter the code here to activate your settings. [Change Settings]
However, I have not received any activation code. The same is true of both accounts.
I have tried using Port 25, 465 and 587 both with and without STARTTLS box ticked. The password is definitely correct. I have even tried activating “less secure apps” in Gmail. Both businesses have a Gmail for Business account with a custom domain name attached. I’m using smtp.gmail.com as the host name. Am I missing something? Do I need to add something to my SPF, DKIM or DMARC records?
587 with STARTTLS should be the correct combination, but I know Google are gradually phasing out the ability to do SMTP authentication with a plain username and password. They want everybody to move over to two factor authentication, and OAuth2, which is indeed more secure. QuickFile doesn’t support OAuth2 for SMTP but there is an alternative mechanism.
If you haven’t already then you should set up two factor authentication for your Google account, then once that’s in place you’ll get the option to generate an app password that will work with QuickFile for SMTP.
I did activate 2FA to try this as I had seen another post talking about this alternative mechanism, but upon activating 2FA I could not see the App Password option. Any chance you can provide a screenshot or guidance as to where exactly I might find this setting please?
EDIT: For those of you that were unable to find the App Passwords option after activating 2FA like me, you need to enter “app passwords” in the search function at the top of the page which will then reveal a link this setting. I was then able to generate a password for QuickFile and use that successfully as described by @ian_roberts , thanks Ian. If you still don’t have this setting option then you will most likely need to remove any registered PassKeys from your account. If this is your Android phone, then you will need to click the link to Sign Out.