Getting error when using smtp-relay.gmail.com in pocketbase

[gaganbiswas]

I have set up my app password as mentioned by @ganigeorgiev in another forum and used the same in the mail settings of pocketbase. I am getting an EOF error while trying to send test mails. What is going wrong here?

Instead of using smtp.gmail.com (this works). I am using smtp-relay.gmail.com.

[ganigeorgiev]

I remember testing the steps from #458 (comment), but it's been a while and it is possible that gmail may have changed something.

Could you post the exact error? Why do you need to use smtp-relay.gmail.com instead of smtp.gmail.com? Is it for rerouting outgoing emails? If it is for rerouting unfortunately I'm not familiar with this setup and I'm not sure whether there are any extra requirements that the client/domain need to satisfy.

[ganigeorgiev]

Are you sending from the same domain and server? You can also try to start the executable with --debug to see if there are any more detailed errors logged in the console/stderr.

I don't think I can help you debug it further because it seems that you need a workspace/enterprise account to use the relay gmail service. I have no idea why it would work with python and not with Go if the same configuration and domain setup is used.

Googling for the smtp-relay, I also found this post - https://www.cubebackup.com/blog/how-to-use-google-smtp-service-to-send-emails-for-free/ (look for "Method 3: Using Google Workspace SMTP relay service."), that contains detailed steps how to enable and configure the relay account.

[gaganbiswas]

Are you sending from the same domain and server? You can also try to start the executable with --debug to see if there are any more detailed errors logged in the console/stderr.

I don't think I can help you debug it further because it seems that you need a workspace/enterprise account to use the relay gmail service. I have no idea why it would work with python and not with Go if the same configuration and domain setup is used.

Googling for the smtp-relay, I also found this post - https://www.cubebackup.com/blog/how-to-use-google-smtp-service-to-send-emails-for-free/ (look for "Method 3: Using Google Workspace SMTP relay service."), that contains detailed steps how to enable and configure the relay account.

All the steps from the above blog are already being followed, since i am already using it in my python bulk mailer app. I will look into the debugging part and if I get something will let you know. Thank your for your quick replies 😄 . I will let you know once I get something useful from the debugger.

[ganigeorgiev]

I think this is caused by the EHLO/HELO configuration because we use localhost as noted in #458 (comment) and #439 (reply in thread), which when using the gmail smtp-relay fails because it seems to require a proper domain name.

I don't have an account to confirm that this is the case but I found a similar issue in the mail library we use - domodwyer/mailyak#79. I'll consider adding a mailer config option with the next release to specify an explicit local sender part.

[ganigeorgiev]

@gaganbiswas I've added in the develop branch (b2ac538) a new "EHLO/HELO domain" field and it will be part of v0.18.0 (there are no ETAs yet).

I don't have access to paid workspace/enterprise account to test the Gmail SMTP-relay, but based on domodwyer/mailyak#79, I suspect that this is the same case.

[gaganbiswas]

Thank you for considering the issue. Will be waiting for the v0.18.0 release. Meanwhile if I get my hands on any workspace account I will be sharing the same with you for helping you out to test the same.