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Why can't I connect to google's smtp server from my droplet after upgrade?

Posted on June 17, 2025

I’m running a forum that sends email alerts, and since June 14th, when there was some server maintenance, I’m having trouble with my application. One issue I’ve tracked down is that it doesn’t seem to have access to Google’s smtp server?

From my laptop:

telnet 172.253.63.109 587 Trying 172.253.63.109… Connected to 172.253.63.109. Escape character is ‘^]’. 220 smtp.gmail.com ESMTP 6a1803df08f44-6fb35c31657sm62737786d6.64 - gsmtp

From my droplet: root@ubuntu-s-1vcpu-1gb-nyc1-01:~/sanity/peculiarForum/backend# telnet 172.253.63.109 587 Trying 172.253.63.109…

Connection times out.

I’m also having some issues with it just running generally slow, so it’s taking so long to load my database the container gets stuck in a healthcheck loop on startup.

Are these things that will settle out with the maintenance or do I need to make changes? My application is down right now.



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Hey 👋

Yep, SMTP ports like 587 are blocked by default on new accounts to prevent abuse. Even though you’re using authenticated Gmail SMTP, the block still applies.

https://docs.digitalocean.com/support/why-is-smtp-blocked/

Your best bet is to either:

  • Reach out to DigitalOcean support and ask if they can review your account and unblock it (they don’t always do it, but worth a try). It might be ok in your case.

  • Or use a service like SendGrid, Mailgun, or Postmark, much better for deliverability anyway. They allow SMTP over API, which is a good workaround and better for performance too.

Some SMTP providers also support alternative ports like 2525, so you might want to check if Gmail does (last I checked, it doesn’t, but maybe worth double-checking).

Let me know how it goes!

- Bobby

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