Cloudron Mailserver mail sent to spam in Gmail

[humptydumpty]

Hi all,

I'm using Cloudron's mail server for sending out mail. I have set up SPF, DKIM, & DMARC but for some reason my mail end up in Gmail's spam folders. Yesterday, I added my domains to Google's Postmaster page. My server isn't blacklisted according to online lookup sites. What could be causing this?

[robi]

Sometimes novelty, if it's a new mail server. Not enough data about the IP/emails sent hence it looks like a fly by night system. ;-/

[p44]

@humptydumpty Yes, me too I'm fighting with this problem... I don't know why... and also, I don't know how to manage.

Also plain text email go in spam folder...

[jdaviescoates]

Sadly this is very common. I think pretty much the only thing you can do is to keep marking them as not spam (that's what I did and now they don't go into spam as often). Either that or use one of the email relay services.

[humptydumpty]

@jdaviescoates This doesn't make sense though. It's like we're being forced to use big tech solutions or get thrown under the bus. If I have all the proper records set up with a clean server IP and sending score then they should go to the inbox. You wanna know what's really funny? I receive 5-10 spam emails per day from GMAIL accounts and they come right into my inbox.

[humptydumpty]

@robi Any idea how long would it take to build enough history?

[jdaviescoates]

@humptydumpty said in Cloudron Mailserver mail sent to spam in Gmail:

It's like we're being forced to use big tech solutions or get thrown under the bus.

Correct

[robi]

@humptydumpty
the idea is to send a bunch of mails to gmail, yahoo, etc.. and get replies, so they get more data about bi-directional communication from your domain.

[marcusquinn]

"lemwarm" is an option

[humptydumpty]

@robi I'll get right on that. Thank you.

@marcusquinn I can't believe services like that exists. But I might have to use it if all else fails.

I dug a bit deeper and came across some interesting posts:

https://serverfault.com/questions/709736/how-does-dnswl-work-how-can-i-gain-better-trust

I visited DNSWL.org and registered for listing my domain and IP with them.

I ran a multi-RBL check against my server IP on Anti Abuse (http://www.anti-abuse.org/) and found out that SpamRats had it listed for spam. I just submitted a request for removal.

Now that I think about it. I regret getting rid of my old DO server. I've been using that for years and didn't have these issues. I should have used the new server as a transitional server while I installed Cloudron on the old one. Lesson learned.

[marcusquinn]

@humptydumpty Yeah, it exists because of a combo of the unscrupulous abusing the privilege of email sending, and because email marketing competes for attention and budget against other types of advertising sellers that also happen to dominate offering "free" email services and are very efficient and gatekeeping "their" audience. Annoying but that's the price of freedom sadly.

[girish]

You can check by sending email to https://www.mail-tester.com/ to double check all the setup. If that's all good, that's the best one can do. Everything else is on the gmail side, which is a black box One thing I have had luck with is to send email to 10 of my friends and have them reply back to me and mark my mail as no spam. Usually, that works.

[humptydumpty]

@girish I got a 10/10 with one yellow "Your message does not contain a List-Unsubscribe header". I don't send bulk emails from my server so I guess it doesn't apply to me. I've been sending emails from the server to my gmail accounts for the past hour and removing them from the spam folder and replying to each one. I think it's starting to work but now I have to test other providers like hotmail and yahoo.

[p44]

@marcusquinn said in Cloudron Mailserver mail sent to spam in Gmail:

lemwarm

Hello Marcus, thank's for this advice. Did you use this service before?

[marcusquinn]

@p44 Actually found a better and cheaper once since:

Obligatory referral link: https://app.warmupinbox.com/sign-up?code=zqCD59w

[p44]

@marcusquinn Thank's Marcus, Warmupinbox seems to have more clean UX and deeper focused on the final purpose. I'll take a look!

My idea is to allocate two-three IP from some VPS, even If I don't need, and keep for future use to "clean" their IP's.

[marcusquinn]

@p44 Its also handy when creating a new VPS or Floating IP to check the IP reputation for bad history before using it. Only takes a few minutes and often quicker to just delete the VPS or floating IP and get another one than jump through all the spamlist delisting hoops.

[p44]

@marcusquinn Thank's Marcus, I'll follow your advice to check the reputation BEFORE, and if reputation is poor, just delete and purchase new one.

Should be interesting that ISP's do themself this control and tell BEFORE the IP reputation.