Stop my emails landing in junk/spam folders

January 2, 2022 6:42 AM

My emails consistently land in my friends and clients' junk folders. Even my own emails to myself sometimes land in junk, despite adding myself and all my addresses to my contacts. Besides this being infuriating, it is impacting my relationships and my business. How do I prevent this from happening?

I have three email addresses under my [lastname].kim TLD. My email is hosted by Gandi.net and my website is hosted on Squarespace. I've followed all the best practice basics I can find, but I'm at a loss about what next steps to take to increase my sender reputation and prevent this. Can someone with relevant expertise explain why might this be happening what my best options are please?

I'm willing to change EMS or adopt some security and reputation enhancing measures, very much less willing to move away from Squarespace or change my domain name. Thanks!

posted by iamkimiam to Computers & Internet (9 answers total)

Best answer: tl;dr Consider moving away from Gandi for mail hosting to a more trusted sender like Fastmail. You can keep your domain, and I haven't had the same types of problems with mail going to spam using my own domains and Fastmail.

Feel free to memail me for my email address if you like and you can try sending me a message, I can shoot you the headers and see how Fastmail spam filtering rates your email.

More detail

Where the website is hosted shouldn't impact whether your email winds up in spam folders. The email host will have an impact. Gandi may have a poor score / may be blacklisted outright.

When your own emails land in the junk folder, do you see any information as to why it's being directed into the spam folder?

If I look at some of the headers for emails filtered into Spam on Fastmail, for instance, I see:

X-Spam-known-sender: no
X-Spam-sender-reputation: 0 (domain; noauth)
X-Spam-score: 3.6
X-Spam-hits: BAYES_99 3.5, BAYES_999 1.2, DCC_REPUT_13_19 -0.1, FROM_LOCAL_NOVOWEL 0.5,
HTML_MESSAGE 0.001, ME_SC_NH -0.001, ME_SENDERREP_DENY 4,
RCVD_IN_DNSWL_HI -5, RCVD_IN_MSPIKE_H3 0.001, RCVD_IN_MSPIKE_WL 0.001,
SPF_HELO_PASS -0.001, SPF_PASS -0.001, USER_IN_DEF_SPF_WL -0.5,
LANGUAGES fr, BAYES_USED user, SA_VERSION 3.4.2
X-Spam-source: IP='95.216.194.37', Host='mxout1-he-de.apache.org', Country='FI',
FromHeader='org', MailFrom='org'
X-Spam-charsets: plain='us-ascii'

If you look at the message source and look for headers with Spam it may give you some ideas why your mail is being rejected.

For example, BAYES_999 is the score for Bayesian filtering - whether the message body "looks" like spam.

ME_SENDERREP_DENY is a "reputation" score for the sender. Likewise, RCVD_IN_MSPIKE_H3 and RCVD_IN_MSPIKE_WL are checks to see if the sending mail server has a good / bad reputation or is whitelisted by the Mailspike service.

See Fastmail's spam filtering page for more info.
posted by jzb at 7:34 AM on January 2, 2022 [9 favorites]

Best answer: In addition to the above: at work (where I manage the public contact inbox) I will sometimes get emails from normally trusted domains sent to spam if the sender embedded multiple links in the body of the email. That seems to be the common factor when people call us up asking why we never responded to them.
posted by showbiz_liz at 7:39 AM on January 2, 2022 [4 favorites]

Best answer: I'm afraid that it could also be simply your gTLD. ".kim" is not one of the absolute worst but it seems to show up in lists of unsafe domains (overview). I realize you don't want to move domains, but I'm mentioning this because at one point I had a mailing list on an ".xyz" domain (which is similarly iffy) that I just eventually had to move elsewhere, and I abandoned the domain name. Stuff was certainly getting spam filtered for that reason with no recourse/solution, but it was even worse in that it's not uncommon for some of these gTLDs to be blocked in entirety -- the last straw was when my work firewall blocked all of ".xyz" (and I unfortunately think rightly so).
posted by advil at 7:48 AM on January 2, 2022 [3 favorites]

I was about to offer a Fastmail spam header analysis as well, but jzb beat me to it. In your shoes I would definitely go that route; there's no point guessing what might be going on when Fastmail will almost certainly give you chapter and verse.
posted by flabdablet at 10:12 AM on January 2, 2022

Response by poster: Thanks, everyone! This has given me a lot to work with. I'm definitely going to move away from Gandi, considering Fastmail, ProtonMail, Office 365 (already have a subscription), or Google Workspaces (to be able to use Google docs/sheets with my email address).

Also going to stick to anchored links instead of direct, and fewer of them! (not everything needs to be like a MeFi post)

Will consider changing my domain name as a last resort if all else fails. It'd be a major undertaking that I can't even process right now.

Thanks again, any other info and ideas still welcome too.
posted by iamkimiam at 10:50 AM on January 2, 2022 [2 favorites]

I've run mail servers for a few small-to-medium sized businesses, and what I learned is that you should just find somebody who can already deliver mail reliably and pay them to do it. Spam filtering (like the SpamAssassin headers pasted above) is based on a combination of content analysis, sender authentication (things like Sender Policy Framework [SPF] and DomainKeys [DKIM], and DMARC, which builds on the first two) and sender "reputation," which includes not just the domain name but the IP address of the server. Even if your own server is well run, if it's in the internet equivalent of a seedy neighborhood it will get a bad reputation by association. Companies specifically in the business of email delivery should have good "reputation" scores and will probably also take care of the sender authentication bits for you.

Also consider using a mailing list manager (like podcast-favorite Mailchimp or Constant Contact or similar) for your marketing messages, and only use your own sender for individual messages related to transactions and support. Sending one message that CCs or BCCs a bunch of recipients is a ticket to the spam folder.
posted by fedward at 11:13 AM on January 2, 2022 [2 favorites]

You should also do some research on SPF and DKIM. SPF is used to identify which servers/domains are allowed to send email on behalf of your domain. Looking at the SPF record for the domain in your profile, the TXT record (which is where SPF is published) is "v=spf1 include:squarespace-mail.com ~all". This indicates that mail delivered by squarespace is legit, and mail from any other sender is a "soft fail", which recipients should be skeptical about. Since you use Gandi for email, you should probably have an entry in there for those mail servers as well -- this could be triggering the spam filters all by itself. Given that Gandi is the registrar and providing the DNS for that domain, it's a bit strange that it's not already there, but Gandi should be able to help you fix it. (Did squarespace ask you to change this at some point to send email on your behalf for a mailing list or something? You may need to have multiple entries if you send emails from multiple places/servers/services.)

I don't understand DKIM very well, but I believe it's a a way to sign each outbound message such that the recipient can validate that it came from someone associated with the domain. Your email provider should be able to help you get this set up properly, but again, if you use multiple services to send email, you'll want to ensure you account for all of them.
posted by yuwtze at 11:32 AM on January 2, 2022 [2 favorites]

Best answer: When I had a problem with my email address, I used mail-tester.com which runs an email you send through a range of tests.

(My problem turned out to be a mis-configured SPF record which was causing emails to be flagged as spam)
posted by mr_silver at 11:04 AM on January 3, 2022 [3 favorites]

Response by poster: I migrated to Fastmail today and it's great so far. I love their 1Password integration too, how neat.

Thanks everyone for all the advice and support!
posted by iamkimiam at 11:59 AM on January 11, 2022