A reminder that a good email filter may be catching the occasional gem

I’ve been very pleased with Gmail’s spam filter. It does catch the occasional item that I want, but that risk is more than offset by the junk that I don’t have to see at all.


Your Email Spam Filter Is More Aggressive Than You Realize

Many people complain that their messages are suddenly getting caught. Here’s what’s going on.

Angela LashbrookFeb 7 · 7 min read

AsAs a freelance writer who conducts many interviews with academics and other experts, I send a lot of cold emails. This takes a fair amount of time and effort, particularly since only about 20% of the people I reach out to ever write back.

That response rate used to be a bit higher, but a few months ago, I got a disappointing message in my own inbox from an expert: My first email, she said, had gone to her university email spam folder. Had I gained some kind of reputation as a horrible writer? Did everyone hate me? Had I been put on the universal academic blacklist for journalists who are total idiots?

Thankfully, no. Instead, for some unknown reason, various email servers had been funneling my messages into people’s spam folders. Since her initial message, the problem has only grown: Not only have I been personally and professionally screwed by spam filters, but I’ve found important, timely messages from other people hidden away in my own spam folder.

I set out on a mission to figure out what the hell was going on and how to fix it. It was, unfortunately, nearly impossible.

According to the cybersecurity company Trustwave, as of 2018, the percentage of inbound email that is spam dropped to 39% — a relatively steady decrease from its high of 85% in 2008. Spam itself, however, seems to be getting more dangerous, as a full 26% of it is infected with malware. To protect users, spam filters have gotten more strict — but are catching a lot of legitimate emails in the process.

“I’ve noticed that my work emails have been going to spam quite often lately — even those addressed to authors I’m promoting,” says Allison Paller, a book publicist in New York. She isn’t sure if it’s because of the marketing and publicity language she uses, or something else entirely. She’d suspected it was happening for awhile, because people kept requesting information from her that she had already sent. But she only confirmed her hunch when it interfered with her promotion of an author.

“He wasn’t getting any of my emails, so he thought I was ignoring him. Eventually he checked his spam folder and, voila, weeks of email from me,” Paller says. “It doesn’t exactly help my underlying anxiety around emailing and feeling like I’m bothering people.”

Peter Lopez, owner of the tech support company Brooklyn Tech Guy, has also been confounded by the problem.

“It happened very rarely a little over a year ago, and then it happened in March,” says Lopez. “And then it happened in May. Then it happened in June, July, August, September, three times in October. It’s a growing problem.”

Andrew Ricci, principal at the public relations and content strategy firm Riccon Strategic Communications, says a similar situation has caused him major headaches at his job. He had a client, he says, whose emails repeatedly and for no apparent reason ended up in his spam filter. “I tried everything, repeatedly adding to safe senders, marking as not spam, everything. Eventually he started sending everything to both my business mail and my Gmail and demanding that I acknowledge every email as soon as I got it,” he says. Eventually, he had to disable his spam filter entirely. “Now I just have to be super vigilant because I get a lot of phishing emails that look like billing notices from Microsoft, Quickbooks, Squarespace, and others that used to get filtered out.”

Though to my knowledge there are no official public numbers on the growing tendency for email servers to classify legitimate emails as spam, a thread on Google’s support forum, from a Gmail user whose emails frequently end up in people’s spam folders, indicates that the problem is not isolated to the few people I talked to. When I reached out to Google asking to be connected to a member of their anti-spam team, I was forwarded a link to an FAQ that mostly addresses spam issues for bulk senders and users with their own domains.

Many people with business emails use hosted email providers with custom domains that, in turn, use either G-Suite (Google’s email server) or Office 365 (Microsoft’s email service provider) to send and receive email.

“It’s very difficult to second guess the algorithms that these spam filters use because the whole idea is that they don’t want spammers to be able to bypass the filters.”

But I don’t. As a freelance writer with a limited business budget, I rely on a free Gmail account. According to Roberta Piket, founder of the tech support company New York Geek Girls, that might be a mistake.

“Those kinds of emails are disposable. So it’s easy for people to set them up and use them for a while until they get tagged as a spammer,” she says. “Then they get another email address, so that those kinds of free email addresses are always going to be under suspicion.”

Getting my own domain, and setting up my own protections to ensure my IP address and email aren’t being used to send spam, will make it more likely that my emails won’t be filtered into people’s spam folders. Indeed, when I did a spam check at isnotspam.com, a site that checks whether an email address is being flagged as spam, I discovered that the IP address for the Google server that the company uses to send email from my personal Gmail account had been flagged by multiple spam filters as problematic. This might mean that someone else whose Gmail is sending from the same Google server as mine is sending spam, affecting everyone else Gmail has assigned that address and making it more likely that our recipients will never receive our mail.

Andrea Kayal, the chief marketing officer at tech support company Electric, says I should try to fix the problem first by being hypervigilant about the content of my emails. I sent her a screenshot of one of the emails that had been flagged as spam, and though it wasn’t rife with issues, she says there are a few things I can do to decrease the likelihood it’ll get caught in a filter.

Optimizing my subject lines is a good first step, she says. The one I often use when reaching out to sources — “Press request” or “Press inquiry” — might seem spammy either to the filters or to the recipients, who may flag any message they see with similar subject lines as spam, thus increasing the likelihood that the server will interpret my future messages as spam as well. A more personalized subject line, like “Your study in Computers in Learning Behavior,” might encourage the recipient to open my email and even respond, thus increasing my reputation with the server. Email accounts with low engagement — those where only a small percentage of recipients open and respond to messages — are also more likely to be flagged.

I suspect this may be part of my problem, as so many of the people I reach out to don’t respond. This could be for any number of reasons: They’re too busy to take my interview, they don’t think they’re the right person to answer my questions, or maybe they simply didn’t even see my email. Whatever the reason, by not opening or responding to my emails, they could be encouraging spam filters to think my emails aren’t wanted. Hence, a higher chance they’ll get dropped in the spam folder in the future.

The same could very well happen to any of us whose jobs rely on sending a lot of email — particularly to people we don’t yet know. And with the exception of hoping people will engage with our emails in the first place, there’s not that much we can do about it.

Other common reasons emails get flagged as spam include sending emails with links, which I’ve typically done to make it easier for people to know who I write for — I won’t be doing this anymore (sorry!); including images in your email; and avoiding words or phrases that the filter associates with spam, from obvious ones like “double your income” to those that are more baffling and problematic, like “medium” (that presents some problems for me, as you can imagine) or “Nigerian” (extremely frustrating and unfair for anyone who needs to discuss subjects relating to Nigeria).

If you’re tech savvy, or lucky enough to have a company with an IT team, updating your SPF and DKIM records can help ensure that emails are landing in the correct inbox. An SPF, or sender policy framework record, is essentially a list of email accounts that are allowed to send messages from a specific domain. This means that only certain email addresses are allowed to send from the theoretical domain, angela dot com. DKIM, or DomainKeys Identified Mail, is a process in which emails are each sent with a key that identifies them as legitimate. Updating these records can make a big difference in your deliverability if you’re using your own domain, though if you have a Gmail account, you’re out of luck in this regard.

Unfortunately, there’s no clear, easy answer for how anyone with this issue can make sure their emails aren’t being flagged as spam. It’s simply too opaque a system for anyone, even professionals, to say for sure how to fix this problem when it arises.

“It’s really sort of a guessing game,” says Piket. “It’s very difficult to second guess the algorithms that these spam filters use because the whole idea is that they don’t want spammers to be able to bypass the filters.”

My own plan includes leaving links out of my emails, writing slightly cringey and earnest but hopefully intriguing subject lines (“Loved your study about millennial homeownership, Dr. X”), and avoiding aliases, which Kayal says can also land a sender in trouble as it increases the likelihood that someone on the list will click “unsubscribe.” If thatdoesn’t work, I guess I’ll be buying my own domain, which honestly I’ve meant to do for awhile but avoided because of the amount of work and money involved. Mostly, though, I’m going to be crossing my fingers and hoping for the best.

As for everyone else? Please check your spam filter every once in awhile. You never know what kind of gems lurk amid the trash.

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