Some (long) thoughts on emails, filtering, and Sanebox

Finally tried out Sanebox because I’ve heard lots of good things about it, and the short review is “I was very disappointed”. I’m still working through my system, but I wanted to share some thoughts just in case it helps somebody else.

First, Sanebox.

I’ve heard about it on podcasts for a long time, and I just recently decided to give it a shot. The idea of having a back end system learn from my behavior sounded very appealing. So I signed up.

It has a couple of really, really good things about it, the primary one for me being the “SaneTomorrow”, “SaneNextWeek”, etc. folders. Drag a message into one of those folders, and it disappears. It shows back up in your inbox at the appropriate time tomorrow, next week, etc. as if it just showed up. That’s pretty cool, and is the biggest “plus” it’s got going for it.

I didn’t play with it long enough for “SaneNoReplies” to really get tested, but I would imagine that would be pretty cool as well. It auto-monitors for replies to messages you’ve sent, and if you don’t get one it lets you know.

As for the cons, there’s one minor one and one huge one.

The minor one is that the pricing page is either confusing or misleading - I’m not sure which to call it. They’ll say the basic plan gives you “two features”, and the middle plan gives you “six features”.

I would think that “SaneTomorrow” and “SaneNextWeek” would be one feature, because they’re both logically part of the category “defer your email until the future” - but they’re not. They’re two separate features. Basically, every separate folder SaneBox creates is a “feature”. Which means that if you want to do much of anything, you get to plan on spending $36/month.

That by itself wouldn’t have stopped me though. The biggest drawback for me - and the thing that stopped me in my tracks - was the ham-fisted way it handles filtering.

For background, I get a TON of email from a server I manage. Much of it is advisory in nature, and doesn’t really need to be read - but it’s important occasionally as a paper trail if something weird happens as it contains information the logs don’t. Some of this email is “you really need to look at ______” sorts of stuff. And some of it is “there’s a problem, right now, that you need to handle”.

Usually I filter it using MailMate filters that sort through the various types and file them away appropriately, so no big deal.

But if I shut off my local filters and leave it to Sanebox, Sanebox can’t differentiate. It all comes from the one server email address, so it’s all the same to Sanebox. I dragged a notification email into the “SaneLater” folder to see how the filtering worked, and all of a sudden everything from the server goes in that folder.

It’s not Bayesian. It’s not ML-based. There’s no intelligence. It’s strictly “email from sender x goes in folder y”.

I realize that not everybody has a server they need to sort through emails from, so maybe a more practical example.

I have a folder called “Paper Trail”. It’s where all of my receipts and super-important stuff goes. So I put some of my “Paper Trail” into a “SaneReceipts” folder, to see how that works.

And again, every message from that email address goes into SaneReceipts. So for a company that sends bills, receipts, support tickets, and company news from a “noreply@asdfcompany.com” address, getting your bills and receipts to file also requires that you auto-file every support ticket and company newsletter as a receipt.

Did some digging. They do offer subject line filtering, but not based on sender and subject - and you have to log into their website to do that. So it’s as hard (or harder) than just setting up a local mail rule.

For that reason, I’m abandoning Sanebox for the moment.

What I’m doing instead, at least for the filtering side…

I use MailMate, so I’m digging much more into the automation rules. MailMate allows you to have complex logic in rules, so I can do things like:

If the message is from x, with a subject line containing “your receipt”, file it to “Paper Trail”.

but I can also do things like:

If the message is from x, y, or z, with a subject line containing either “your receipt” or “your bill”, file it to “Paper Trail”

This lets me quickly differentiate the stuff that has to be auto-filed. But MailMate also lets me come up with smart folders that have their own rules, which trigger as soon as a message becomes available to that folder.

As an example, I made a folder called “7 Days”. If a message is over 7 days old, it shows up in that folder and the folder’s rules trigger.

This means that some newsletters that I want to get, but might not have time to read that week, can be auto-deleted or auto-archived. Or if I get busy with something and my notice that my Amazon package was delivered is still sitting in my inbox, I can just auto-archive it out of there after a week.

There’s a surprising amount of email that can be dealt with this way, and it helps keep stuff from piling up in my inbox. I’m highly distractable, so that can be a real problem.

MailMate also allows me to make my own “blackhole” folder. If I tag a message as “blackhole”, I have to keep that message, but future messages from that sender can be auto-deleted via an inbox rule.

I definitely don’t have it all figured out yet, but it’s an interesting journey. I’m still playing around to see if there’s a reasonable way to mimic Sanebox’s delay feature - but I also get the feeling that email might not be the way to fly with that. I’ll post back if I figure something out.

Anyway, those are my thoughts - such as they are. Hoping that maybe this might help somebody thinking through their email overwhelm. :slight_smile:

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I have to say that gmail is pretty good. They have a Snooze feature, that works just like your SaneTomorrow or SaneNextWeek. You can also setup pretty complex filters. I also find their spam filtering to be very good.

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If Gmail was pure IMAP, I’d probably still be there. Their weird behavior where messages can existing in multiple folders with pointers saying “that’s me over there” - resulting in deletion of messages not always actually deleting the message in question - was super-confusing to me, so I bailed probably 8 years ago. :slight_smile:

You are not alone. I’ve had to explain to several people that all Gmail messages reside in the same folder. And that Inbox, Sent, Spam, etc. are just tags. I’ve found it helps some people who use folders to hide the “All Mail” folder.

AFAIK Gmail has most, if not all, of the same features as SaneBox. It even nudges me to follow up on messages I have sent or received automatically.

But I can definitely see where SaneBox would be a big help to people who don’t have good server side rules.

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Yeah, hiding “All Mail” helps, but it’s mind-blowingly frustrating to go through and do all the work to actually clean out a mailbox and discover that all you did was clean out pointers to the messages that are, in fact, still on the server.

Will Google let you do things like resurface an email next Monday, or tomorrow morning, or next month?

Interesting re: each SaneLater folder being a feature. I agree that’s misleading on the pricing page, though I guess you’d probably figure it out during the trial.

What were you looking to do, since MailMate already had everything working for you? If it was just a couple of snoozes, it seems like one of the cheaper SaneBox plans would work well in conjunction with MailMate rules.

Yes, that’s available in both webmail and the mobile app. (see below). If you have “Nudges” turned on it will frequently prompt you to follow up or reply to messages automatically. This appears to be triggered by the content of your message.

Gmail automatically sorts your mail into Social, Updates, Forums, and Promotions. And you can have these categories presented as separate Inboxes if you prefer. But I don’t since I work almost exclusively on mobile and like to keep things simple.

snooze

At the time of trying it, I didn’t have as much worked out. I was thinking that the “snooze” stuff would be fun, but I was really hoping for a more “drag & drop” sorting setup.

Basically, I was hoping that Sanebox would be more like a spam filter that learns and adapts based on sender, subject, content, etc. as it goes. I use SpamSieve, and it occasionally gets it wrong - but I just move messages in and out of Junk and it learns over time.

But that’s not anywhere near what it does. It basically says “oh, you moved a message from Dave into SaneLater. Got it. Everything from Dave goes into SaneLater now.”

And its “reminder” feature was another thing I was looking into. I thought it would act more like the other folders, where the original message would come back, but in reality it just generated an email from Sanebox with the text body of the message attached. And when I say “text body”, I mean just that - the PDF agenda attached to the original message, which I forwarded to Sanebox, was stripped out of the message. So at the time of the meeting I got the reminder - but had to go dig through my email to find the document I needed for the meeting, which is the exact behavior I was trying to avoid by using Sanebox.

It just didn’t do much of anything quite like I expected.

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This is exactly why I never took Sanebox any further. None of the features were what I would have called Smart, and I could recreate them using Mail rules or email clients (E.g. Snooze until tomorrow)

The Sane Black Hole especially was massively disappointing, I was expecting some form of learning. Not just filtering by sender.

For the monthly cost, I expected so much more.

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Gmail is excellent once you “get it” - snoozing, nudges, rules, spam filters, prioritisation … all excellent.

Biggest weakness is the lack of a desktop client. I use it with Apple Mail which works fine but means I don’t have access to these features on the desktop. Any recommended client applications for (Intel) Mac that do allow access to them?

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Have you looked into Gmail or Fastmail filtering?

These would be semi-manual, of course. But with a bit of love over time, you can fine-tune the filters (and the order in which they’re processed) to make sure messages go where they should go.

For instance, I have a few collaborators whose direct messages to me I’ll always want to see. However, we also participate in some of the same mailing lists—their messages to those lists go in my “Reads” folder. I do this with two filters. An earlier filter will put messages including those mailing lists straight into the Reads folder. If a message makes it past that filter, another filter checks if the sender is in my “Screened” contacts group, and if they are it goes straight into my inbox.

Like I said, it takes some configuring to get the order of operations right, but my inbox’s been a much nicer place since I started doing this kind of thing.

I use Apple Mail to go through my Inbox. If I want to use any of the gmail features, I flip over to the web app and use it there. Their web app implementation is good, even supporting keyboard shortcuts like a good desktop app would.

Your experience with SaneBox mirrors mine from a few years ago — in the end I found it more of a hindrance than a help.

In the end, I found out that the way to get my inbox under control was (spoiler) to actually take control of it and put in the work to cut down on unwanted email coming in, archive away the stuff that needs archiving and either deal with or nuke the rest. Switching to MailMate on the Mac really helped in that regard, as did using Fastmail’s spam filtering and other tools.

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I don’t use Gmail because of its weird non-IMAP-compliant behavior. And oddly enough, I do use Fastmail - but I hate the web interface for messing with rules. And some of the rules I have are outright not possible in Fastmail due to their multi-level nature.

Although some of the simpler, more high-volume stuff for the server messages I may move back to Fastmail. That way it would be handled even if my desktop client were offline.

That’s my only frustration with the current system - that some of the super-high-volume stuff doesn’t get handled unless my computer is running. :slight_smile:

Like Microsoft Exchange, Gmail’s default protocol isn’t IMAP. Exchange uses MAPI over HTML and Google uses ??. But, from what I’ve read, both Exchange and Google maintain a connection to the server when using Outlook or the Gmail client.
Bottom line, IMAP is an add-on that allows the use of 3rd party clients.

The protocol is irrelevant to my concern. Google’s method of storing messages means that messages you intend to delete frequently don’t actually get deleted, and if you get used to messages not getting deleted then the reverse is true.

The answer to “I just hit the delete key - what happens to my message?”, with Gmail (at least when I was using it), is “well, that depends on what folder the message is in, whether you’re using an app or the web interface, and how you have certain settings configured”.

Sometimes it would delete the message. Sometimes it would delete the label, and leave the message. And the result is semi-perpetual confusion over what state one’s email is in, and a lot of extra work when you discover that it’s been archiving all the spam you thought you were deleting.

It’s crazymaking.

If other people like it, I’m glad they found something they enjoy. But I’ve had enough problems, and I’ve had enough clients have problems, that I just refuse to use it anymore.

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Say more?

I think it’d be tedious but I bet you could stitch it together.

I’ve never run into that but, should you ever want to try Gmail again, I can assure you that Apple’s mail clients don’t have that problem.

When Ray Tomlinson, or Shiva Ayyadurai, or . . . invented email it was a different time and communications didn’t try to be secure. Since then people have been trying, and failing, to bolt on security. Email is a perfect example of why you have to include security in your original design.

Until someone comes up with a replacement we’re just going to have to put up with the CF that is email.

MailMate will let me do something like this:

For each message
    IF ANY OF
        sender = 'email@domain.com'
        sender = 'email2@domain.com'
        sender = 'email3@domain.com'
    AND
        subject != 'Some Subject'
    AND
        subject != 'Some other subject'
    AND
        message is more than 1 week old
    THEN
        delete message

AFAIK that type of logic isn’t possible with Fastmail.

I could probably do it with a bunch of individual rules, but that’s not very clean. And of course MailMate allows me to do stuff I wouldn’t expect Fastmail to even try to tackle, like:

FOR EACH MESSAGE
    IF
        sender exists in folder 'People to block'
    THEN
        move message to 'Blocked messages'

If you haven’t ever played with MailMate, grab a copy and look at all the crazy stuff you can do. It’s pretty insane. :slight_smile: