Digital Ocean Problem with Email

I'm having some trouble sending emails from Thunderbird through my server on Digital Ocean to Gmail. I'm totally lost. Between DMARC, Postfix, DKIM... I have no clue what I'm doing and it's pretty tough to troubleshoot. When I try to send mail to Gmail it comes back with

550-5.7.1 This message does not have authentication information or fails to pass
550-5.7.1 authentication checks. To best protect our users from spam, the
550-5.7.1 message has been blocked.

I've got SSL, not seeing anything on blacklist reports.. I have no clue what to do. I don't know if I need to fix my MTA through console or what.. Any insight whatsoever would be invaluable to me.

God bless

P.S. One test email got through to spam, but then went back to Mail Delivery Failed. I have cPanel installed on my droplet and I create emails there.. I thought that would take care of all my server settings but maybe it didn't.

I'd really prefer to host via Digital Ocean, but I need to be able to setup working emails for my projects!

I encountered the same problem 2 weeks ago, but I'm still looking for the solution please help

I just went back to Inmotion... It has to do with how the MTA and what not is setup in console. It's too much hassle, plus, I have to pay for cPanel and the savings just aren't worth it. Having 10 extra steps for everything is too much.

EmotionalKnapsack said:

I just went back to Inmotion... It has to do with how the MTA and what not is setup in console. It's too much hassle, plus, I have to pay for cPanel and the savings just aren't worth it. Having 10 extra steps for everything is too much.

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unfortunately there is no trust in such cloud systems anymore. so you have to make extra payments brother

I've hosted with everyone. From Hostgator to AWS. I just want to work on my projects ya know? Not have to lookup a hundred tutorials when I wanna do one thing. It's just easier to go with a reseller account, my WHM, and cPanels with all the voodoo handled by the host. Saves on IT

I would suggest Aws+sendy

Sendy looks pretty good. They seem like they have things boiled down for the consumer.

EmotionalKnapsack said:

Sendy looks pretty good. They seem like they have things boiled down for the consumer.

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Yeah, but we need some time to make sure of that.

It's complex for sure. I love the allure of being totally in control of my servers, but I also like to make money without looking up a thousand tutorials. I'm researching things for clients all the time anyway. So it just makes since for me to keep things simple. Although, when I have more time I'll look in to AWS+Sendy. It looks good... I'll definitely migrate when I hire another IT guy. I just don't want to be in console all day until I learn more about it.......

For seny you can use it from any hosting provider so you can test it without leaving your host

sending emails correctly is a task that increase in complexity every year so It is much better to use a service that do the hard work for you