Email Cleanup Strategies: group/sort, or is there a better way?

The Question
This is a long, post, so I tried to break it up into sections. I hope that helps.
Is there a good way (easy, scriptable, etc.) to do data analytics on a mailbox to simplify cleanup? Here are three examples; there are probably more:

  • group/sort-descending by highest volume senders
  • group by attachment type, sort by size
  • identify messages not accessed in the last x days (maybe with sorting/grouping)

The Situation
Like the rest of us, I often wind up with an inbox full of email. I have (gmail) server-side rules that strip out a lot of it for me, but those now feel like they’re not doing what I want. Today, I had 200-ish items in my inbox and 1500-ish unread items in my archive. This may not seem like a lot to some, but the clutter drives me to distraction. So, I set out to clean this up.

Cleaning the inbox was pretty straightforward. The big problem is the archive. I know it’s the archive, but I can’t stand seeing all those unread items. The best method I’ve found so far is filtering for unreads in archive, then doing a search based on sender to grab a large number of items (including previously read). Then clean up that group of messages I just isolated. Lather, rinse, and repeat.

My Idea/Problem
Searching by sender takes forever. I wish there was a better way to handle this. My first thought was to do some kind of grouping, like group by sender and then sort senders by number of messages they sent. Of course, there’s no easy way to do that.

The Ask
I can probably script up some way to do this, but before I dive down that rabbit hole, I wanted to ask you all how you handle this sort of cleanup. To me, it’s a similar sort of thing I might do to clean up old files in a file system. Then again, this may be a great example of an XY Problem: maybe I’m stuck on the group & filter strategy because it the first thing I thought of and I’m overlooking a better way. Any advice is appreciated.

I’m just beginning to put together a strategy for a family member is also in email hell - groaning inbox, unsorted archive (years!), ancient trash, etc. When I’ve approached this problem in the past I found it was helpful to ask: “all those unread emails and unsorted archive: I’ve managed to live up to now with them unsorted and unprocessed, what value will I really get from processing the backlog? That is, if nothing in that pile is on my radar now, why add it?” So my strategy focuses on breaking the attachment (!) to that already-ignored archive and old emails in the inbox and instead put energy into saving them away where I can find them if by chance I absolutely need to, but otherwise unburdening myself of them. So they go in mbox files by year or some such. Maybe keep a year of emails in your active mailbox so it has things you’re most likely to look up. And delete trash older than X days. Then build a system to go forward from that clean slate.

Absolutely agree about breaking attachment to “infinite email storage.” I discovered email in college and was forced to deal with limited mail quota. Gmail at the time was a breath of fresh air, but now it’s gone stale.

I’m happy to get rid of most of my archive and I’m working in that direction. The problem I think I have now is that I have lots of incoming mail that I’m potentially unaware of. For new mail that hits the inbox, or gets filed (why do I file it if only to delete it later?), I have a couple of goals:

  1. Identify the mail I really care about (improve signal/noise ratio)
  2. unsubscribe or otherwise kill mail that I don’t want.

As I look through my archived unreads, They’re mostly in category 2, but there are a few items that I need to see and possibly act on. I need to find those in the pile. I suppose another way of stating my original problem is that unique or infrequent senders are more likely to be valuable in the general case.

So archive is going to have

  • a few hundred emails that I really need to keep (these probably belong in DEVONThink or another non-mail filing system)
  • a ton of old stuff to purge

And inbox is going to have

  • tons of permissive marketing spam to eliminate (unsubscribe, blackhole, etc.)
  • announcement/update spam that I potentially care about or need to act on, but with a short shelf life (act on it, save for a bit, delete)
  • actual correspondence that I’ll want to archive (again, to DEVONThink)
  • records like receipts, etc. (DEVONThink)

I suppose I could use some broad category labels to identify those categories and maybe some scripting to purge things on some sort of retention schedule. It wouldn’t solve my immediate problem but over time I’d approach the end goal.

One related thing I’d love to be able to do: Set mail rules to delete specific kinds of messages a certain amount of time after receipt.

Most of these are newsletters (no need to have the digital equivalent of that pile of National Geographics in the attic) or marketing/sales emails (I might want the most recent one or two, but that’s about it)…

Suggestions welcome! I’d prefer not to use server side rules – I can’t really run my email through someone else’s servers.

1 Like

A simple way would be to create Smart Mailboxes that categorises the message by Subject, Sender , Contact Group etc where the received date is > X number of days ago. You can the highlight the messages and Delete in bulk.

A simple one I use is for Social Media (sender contains Twitter, Facebook etc).

I am sure I could automate it via AppleScript though given the chance :grinning: