Emails sent through Google SMTP going to spam

Hi there i have been having the same issues with my clients invoices going into their spam/junk mail.
i then was advised to change the settings so that invoices would go through my gmail.
this works fine for about 3 weeks and then all emails go into spam again,
Finding this very hard to deal with as i am receiving complaints from clients.
Either the fault is with google 3rd party or Quickfile settings.
the messages i receive below are
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…

Again in a few weeks the same thing happens again.

Hi @Oneillms1

If the emails are going through Gmail, then Google is the sending server and the issue will be on their end causing the emails to go to spam.

Are you using 2 factor authentication with Google? If so, are you using an app password with QuickFile? Have you changed your Google password recently?

Hi thanks for reply.
When i notice invoices are going to spam. i check the SMPT settings is then in error and i receive the message above. so the link is lost between Quickfile and google.
I didn’t change any password.
2 factor is on when i hot accept on my phone.
Thanks

If you’re using 2-factor authentication, please ensure you’re using an app password for QuickFile with your Google mail account (this includes standard Google accounts, and Google Workspace, too). This is required to access the mail inbox and your standard password will not work in this case.

Regarding the spam, I have noticed a few issues with your SMTP setup and will drop you a private message with some details so you can look at getting these fixed to improve deliverability.

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