I have set up the action_mailer_optional_tls gem on my Rails 2.3.2 application running Ruby 1.8.6, but I’m running into issues when trying to send emails through Gmail’s SMTP server.
Whenever I attempt to send an email, I keep getting this error message:
530 5.7.0 Must issue a STARTTLS command first
It seems like there’s a problem with the TLS configuration, but I’m not sure how to fix it. The gem is supposed to handle optional TLS connections, but something isn’t working right.
Has anyone managed to get this gem working properly with Gmail? I’m wondering if there are specific configuration settings I need to adjust in my mailer setup. Any help would be greatly appreciated since I’m stuck on this issue.
hey, i had the same problem! just enabling STARTTLS auto did the job for me. also make sure ur using port 587, not 25. that really helped me out. good luck!
This Gmail SMTP error pops up frequently. I’ve encountered this specific configuration before, and it’s crucial to set your TLS options in the ActionMailer config. Ensure that enable_starttls_auto is set to true in your SMTP settings. Additionally, switch your authentication method to ‘plain’ rather than ‘login’, as Gmail can be particular about this. Sometimes, the gem might not automatically handle Gmail’s TLS requirements, so enforcing STARTTLS is generally a reliable fix. Also, verify your credentials, since authentication failures can lead to TLS errors.
Had this same issue two years back with a legacy Rails app. The action_mailer_optional_tls gem gets weird with Gmail’s stricter rules. Here’s what fixed it for me: explicitly set the TLS version in your environment config. Gmail wants TLS 1.2 or higher, but older Ruby versions often default to something lower. Try adding tls: true next to your enable_starttls_auto setting. Also worth checking if your Ruby OpenSSL version actually supports the TLS version Gmail needs - that’s what was breaking mine. That 530 error usually means the connection can’t establish proper encryption before trying to authenticate.