[gpvos]

Don't do that, it will be disastrous for you.

Instead, send them a politely worded one-time announcement with an invitation to subscribe. Clearly mention that if they don't, this is the last mail they'll get from you, and keep that promise by deleting their address. You'll still get some pushback, but I think most people would find that acceptable.

[mrweasel]

At least with your suggestions there's some chance that their newsletter won't instantly get flagged as spam.

I'd do what you suggest, but send the newsletter from an separate domain once subscriptions have been confirmed.

[EGreg]

That one-time announcement is called an email. And therefore that first announcement itself can be flagged as spam.

And naturally, unless they click a link in the first email, gmail should consider anything subsequent to be spam anyway. They have no idea whether consent happened somewhere else or not.

The unsubscribe links must work without even opening the email, according to gmail rules.

[mrweasel]

What I'd be concerned with is that if you have never sent anything to these users, they might have forgotten where and when they gave you their email address and simply mark your message as spam.

We've trained users to not use "unsubscribe" because some spammers once used that to verify addresses, or they may simply click "Spam" because they forgot who you are and think you got their address illegitimately. Gmail also doesn't make unsubscribe as visible as "Spam", making flagging the easier option. So now Gmail will see some percentage of users manually flagging you as a spammer, tainting your sender. This is why I'd switch the newsletter to a new domain or at least a new sender address. That does mean preparing that new sender, give it a bit of time to mature and send a few emails to Gmail accounts you control and ensure that they are not flagged as spam.

Probably also test with a list of Gmail account you control and check if you're tagged as spam and fix that, before doing the big push.

[inetknght]

> I'd switch the newsletter to a new domain or at least a new sender address

Big Red Flag for the spam button: newsletter comes from a different domain than it links to.

Don't switch your newsletter to a new domain. Use your domain, or don't send it.

[e-mail] is totally fine.

[zephen]

As a gmail user who may or may not have had to enter an email address to do something on the web, and who gets annoyed by spam, let me describe my decision points (anecdote is not the plural of data, of course, but here I am) when it comes to "unsubscribe" vs marking something "spam."

If your email reminds me (upfront!) how and when and why I specifically gave you (and not some other third party) my email address, and promises that you are advertising this newsletter one time, and it is opt-in, and you keep your promise, I am highly unlikely to mark it spam.

Now, this presupposes that it was really me who gave you my email address. I have a fairly generic email address because I got on gmail early. There are many variants of it, but sometimes people forget to add the trailing numbers or letters, so I get misdirected email all the time.

If the misdirected email is personal, I usually respond letting them know of the issue.

If the misdirected email shows a clear understanding that I might not have been the one who really signed up then I give them a pass.

If the misdirected email blithely assumes that I am the one who signed up, then I blithely assume that its senders are too fucking stupid to use the internet and it goes straight into the spam bucket. (And this is usually an easy call because they use the name of the person with the similar email address, which is not my name. My email address is [e-mail] and there are many different first names that start with the same initial.)

Any failure on any of those other points starts to increase the likelihood of it being marked spam, and...

> The unsubscribe links must work without even opening the email, according to gmail rules.

So here's where I'm a hard-ass and maybe even worse than google's rules.

If I see the RFC8058 unsubscribe link, it is too late. I only notice that link after I've decided to mark your email as "spam" and google asks if I'm sure, or if I merely want to unsubscribe.

Why did I decide to mark your email as spam? One possible reason is that I read through it, decided that the sender legitimately had my email address and was acting honorably, and then clicked the unsubscribe link embedded in the email.

When I do that, one of two things happens. Either I get some form of "thank you, you've been unsubscribed" or nothing happens because the sender assumes that I am OK with them executing javascript on my computer.

This is a privilege I jealously guard and only reluctantly offer to as few websites as possible.

Even if I previously gave you my email address, that did not come with an open invitation to use my computing resources for your own purposes.

[EGreg]

So by your own description, ANYONE sending you a newsletter, by complying with Google’s rules, they piss you off and make you mark their email as SPAM because, according to you, they made “javascript execute on your computer”. Actually, gmail is the one executing tons of javascript. The mandatory unsubscribe LINK uses HTTP, not even HTML. Google just requires that the unsubscribe instant.

It is an unwinnable situation.

With all respect, why would I care what an impossibly hardass tech person would do if I sent them an email in an unwinnable situation? The vast majority of our users are not this technical, let alone a hardass HN denizen who advertises the fact that the mere compliance with Google’s rules will piss them off due to a misunderstanding of how unsubcribe works.

Here is what we might both agree on: email sucks. You shouldn’t be reachable by anyone who just has your address, and it is not your job to be vigilant. Then all these problems go away.

[zephen]

> So by your own description, ANYONE sending you a newsletter, by complying with Google’s rules, they piss you off and make you mark their email as SPAM because, according to you, they made “javascript execute on your computer”.

Are you deliberately being obtuse, or is it natural? I don't need to use gmail's web interface if I don't want to, but as it happens, I do let google's javascript execute on my computer.

> The mandatory unsubscribe LINK uses HTTP, not even HTML.

Two links are required. One in the header, and one in the email. As I wrote, if I read to the end of the email to make a decision, then I will click on the link in the email. Which often goes to a webpage with javascript on it.

> It is an unwinnable situation.

Did I write that I mark everything as spam? No? Why not, I wonder? Did it ever occur to you that if I am describing when I mark things as spam, that there are things that I don't mark as spam? No? Do you even read what you yourself write? No? You should try it sometime.

> With all respect, why would I care what an impossibly hardass tech person would do if I sent them an email in an unwinnable situation?

With all respect, if you wrongly believe the rules I gave are unwinnable, you shouldn't care. I won't be receiving further missives from you, and nature will take its course in determining whether I was an outlier or the canary in the coalmine.

[EGreg]

To quote your own words:

>So here's where I'm a hard-ass and maybe even worse than google's rules. If I see the RFC8058 unsubscribe link, it is too late. I only notice that link after I've decided to mark your email as "spam" and google asks if I'm sure, or if I merely want to unsubscribe.

The way I read it, this is an unwinnable situation. We must supply this link, in order to comply with Google's rules. If you see this link, it's too late. You're making it as spam. Because I may run javascript on your computer.

Having re-read it, it sounds instead like: you're likely mark it as spam before you get to this link (even though the web interface surfaces the unsubscribe button right in the list of emails -- but you don't use that interface).

Well, I guess there is a narrow path to "victory": mention that it may have been someone else who signed up, then if you see the unsubscribe link, you click it, then I'm supposed to say "thank you" and not serve any javascript. Anything else, and you click SPAM. Or maybe you already did.

[traceroute66]

> Instead, send them a politely worded one-time announcement with an invitation to subscribe.

NO. DO NOT DO THAT !

That is terrible advice and it is against the law.

Opt-in has to be done without inducement and of a person's own volition.

Sending a mail to someone saying "pretty please sign up" is not valid opt-in. It is spamming a bunch of people hoping they will opt-in. It does not matter if you got their mail another way (e.g. if they purchased a product, you can't then spam them trying to get them to opt-in for your mailing list).

One of the fundamental reasons the opt-in law exists is to stop people doing the shit you suggest and ensure that lists are correctly built in a clean manner.

[EGreg]

Under GDPR, can someone send an email to people who 1) downloaded our app, 2) voluntarily entered their email, viewing a message that says if they do that, we can send them a newsletter about how to be more efficient with the app, and 3) selected what kind of person they are, e.g. a teacher, marketer, etc.

But it's been 10 years. Can we send them a newsletter now with an unsubscribe link? Does GDPR have an expiration date on that stuff? Yes it was affirmatively opt-in.

[gpvos]

I'm no expert, but I think that in principle you'd legally be okay. But the 10 years makes it more difficult on a personal level; many, likely most people will have forgotten about you and the permission they gave. Hence my earlier advice.