Fed up with Mac Mavericks Email (tagging, suggestions and more please!)

January 27, 2014 11:06 AM

I'm an inbox zero guy - I'm at my end with Apple Mail. I think I need to move to a new tool - Thunderbird? Outlook? Please hope me!

I'm at my end with Apple Mail, my favorite plugin - MailTags isn't really working right. with Mavericks. (BTW, Mailtags allows you to "tag' messages and then those tags can be used as 'smart' criteria for smart mailboxes.)

I'm try to embody inbox zero (having nothing unread nor using my inbox as a 'holding pen')
I have an iPhone where I glance at my email, but it doesn't help (beyond emergencies.)

The goal is to quickly know my email at a glance.

Here's the way I work right now: A email comes in, it gets checked with a bunch of rules....and put into a some smart mailbox.

1. All spam is removed (in it's own smart mailbox for a 1x a week glance)
2. Then all 'bacn' (that's mailing lists that I want to glance at, but NOT in my main mailbox, looked at 1-2x a day; right now it gets tagged and a smart mailbox gets built from the tag)
3. Then colorize everyone I know (from a certain company, from my address book). A smart mailbox removes anything that is spam or bacn.

So, when I glance at my 'inbox' - I can quickly tell who I know and who I don't with zero clutter.I go through email to answer right away ....or toss into an "action" folder to go through when I have real time.

Mailtags is really failing me at this point (and the developer is 'not sure' when issues will be cleared up. Mail has crashed 5x today (maybe or maybe not due to the plugin.)

Small notes; I have too many email accounts. That's not going to change. It's about 10, with 70% being gmail or gmail for business, an Apple iCloud account and a bunch of comcast POP3 mail (which I could get rid of or filter through another gmail account)

Yes, I'd love to be able to glance at email on my iOS device, and have it integrate - but it's not my primary device; because some responses have to be long and thought out.

I'm looking to hear about other tools you use for mail or how you'd solve my situation - whether it's filtering everything through a particular Gmail account, outlook, thunderbird or something else.

posted by filmgeek to Computers & Internet (15 answers total)

I also like to keep my inboxes clear. I put everything in Gmail or Google Apps or set up sending/receiving in one of those. These accounts have filters set up similar to what you describe. Then, I use Mailplane, which I've liked for a long time. Mailplane 3 came out last year and has none of 2's context switching slowness. I also have Gmail's keyboard shortcuts memorized and turn on display next item after archive so processing is much faster.
posted by michaelh at 11:12 AM on January 27, 2014

Response by poster: michaelah - two questions:

Am I wrong on this - does MailPlane support iMap? Because I need my iCloud address. The other POP (dammit, they are POP accounts, not SMTP as in my post) I could filter through another gmail account.

Second, do you do any mobile viewing?
posted by filmgeek at 11:20 AM on January 27, 2014

I don't think IMAP is supported, unfortunately. For mobile I just use the Mail app on iPhone and look at the combined inbox when I need to.
posted by michaelh at 11:36 AM on January 27, 2014

Might be worth looking at MailMate as a replacement mail client.
posted by StrawberryPie at 11:59 AM on January 27, 2014

Response by poster: I'm looking at:

Airmail, Outlook, Postbox, MailMate, Inky and MailPlane - someone else must have done this sort of pro/intensive comparison before, right?
posted by filmgeek at 12:05 PM on January 27, 2014

I use and can recommend Fastmail + Postbox. I have several addresses at Fastmail, and that's where I set up all the folders and filters. Then Postbox just shows me a nice tidy version of it all on my desktop, and thanks to IMAP my iPhone has the same view. If I wanted it to, Postbox could apply additional filters as it pulls email from Fastmail.

I have a business email address, a personal address, and two newsletter signup addresses (one for general business newsletters and one for newsletters in my niche). I set up something like 17 folders in Fastmail for emails related to clients, products, prospects, travel, etc.

Basic workflow:
- Someone sends email to me.
- Fastmail does an initial spam filter, which works very well. Then:
- If the email is addressed to a newsletter address, it goes to one of the newsletter folders.
- If it's addressed to my business or personal address, Fastmail checks the sender and content and sends it to the appropriate folder or, in the case of a few pests, discards it without me ever seeing it.

Result: Only legitimate email from real people ends up in my in box. Automatic emails like receipts go immediately to their appropriate folder. Newslettery stuff is automatically filed where I can read it at my leisure.

I don't see a way to tag emails in either program, but I can flag emails in Fastmail and they show up as flagged in Postbox. I rely on folders for sorting and prioritizing. One feature I love in Postbox is the keyboard shortcuts to move messages to another folder.

I won't use Gmail because I have a business and don't trust Google. I gave up on Apple Mail because it kept choking and I like the keyboard shortcuts in Postbox. Fastmail has had a couple of hiccups over the (many) years but it has worked better than anything else I've tried.
posted by ceiba at 12:26 PM on January 27, 2014

I have a very very similar workflow to yours, and a similar number of email accounts -- but I do it just using mail's rules to sort everything out into the appropriate mailboxes... Rules can move items into mailboxes, color them, or tag them (sort of: if you use the "mark as flagged" option in a rule you get a choice of seven flag colors, which you can use to filter items into smart mailboxes if you need to). My one minor gripe is that the spam filtering isn't quite robust enough -- I used to use SpamSieve as an add-on, stopped at some point when an OS upgrade broke it, and never bothered setting it up again (though I see now they have Mavericks support, I may have to give it another try...)

It sounds like your main problem is with the "mailtags" plugin rather than with mail itself, and as far as I can tell from your description there doesn't seem to be any reason you need to be using the plugin. Can you clarify what about Mail's rules weren't sufficient for your needs?
posted by ook at 12:52 PM on January 27, 2014

Also have a look at MailPilot - it's one of those inbox zero apps. It will work with gmail/imap and pop. I'd move to MailPilot, but I anticipate that mailbox.app will comeout with a desktop tool eventually - so until then I use mailbox.app on ios and gmail in the browser (I like the tabs in the gmail client when I take a weekend off.)
posted by Brent Parker at 1:42 PM on January 27, 2014

Whoops - I'm wrong about mailpilot supporting POP. It's still a good product though.
posted by Brent Parker at 1:44 PM on January 27, 2014

Response by poster: Let's add in - needs to have integration with OSX address book...
posted by filmgeek at 2:44 PM on January 27, 2014

Response by poster: ook,

I keep everything in the 'inbox' on every tool and use the tags to dynamically build a smart mailbox of spam, bacn, etc.

If I'm on my ios device it sees all of them. Nothing is filed. At this moment I have 112k messages (across the numerous accounts.)

I really, really like mail pilot - exactly there are no rules! I don't want to manually pull out all my mailing list garbage by hand just to file it away...
posted by filmgeek at 7:45 PM on January 27, 2014

I feel you on the smart inbox feature. There doesn't seem to be only one tool that handles all of our wishlist in an email client. But if we are looking at email with an inbox zero spirit, the only things that need to be filtered are the bacn and spam, right? Everything else needs a decision on what to do with it. We file it for later, archive it, or trash it. I look at my bacn folder once a week (tagged automatically in gmail) or so and if I really need to look at on an iOS device, I use the gmail app. Alternatively, you could set up a bacn gmail account - that's a smart mailbox!

Here's my filter for building a bacn tag in gmail that catches 99% of bacn:
((("If you no longer wish to receive communication from us" OR "to stop receiving emails" OR "e-mail options" OR "opt-out" OR unsubscribe OR "viewing the newsletter" OR "privacy policy" OR "enews" OR "edit your preferences" OR "email notifications" OR "update profile" OR "smartunsubscribe" OR secureunsubscribe OR yahoogroups OR "manage your account" OR "group-digests" OR "we respect your privacy")))
posted by Brent Parker at 6:56 AM on January 28, 2014

Thunderbird has read-only access to OSX address book, so it can use it to match addresses or pull info from your contacts for matching in mail filters. It cannot write to your address book. People have been asking for this for years, but so far read-only is where it's at.

Building message filters in Thunderbird is pretty easy using their filter tool. I have a number of filters that sort mail based on sender, subject, or patterns (e.g. sender contains "company.com" or subject contains "Sales" or sender is in my address book "OSX Address Book" and so on and so on).

Available options for filtering are send to specific folder, send to folder in another IMAP account (great if you ever have mail you want to selectively merge into one specific account), mark/unmark as spam or unread, add a star or tag, stop filtering at this junction, delete immediately, etc... the only restrictions are that matching is either "OR" or "AND" for each individual filter, there is no way to match (this OR that) AND (the other thing).

Once you have a basic idea how you want to filter your mail, you can even manually build filters, which might be faster than doing it with the GUI. Filters are saved on a per-account basis, in Library/Thunderbird/Profiles/{profile folder name}/ImapMail/name.of.account/msgFilterRules.dat.

Each individual filter is just a few lines of text. For example my filter for daily junk from a specific company is something like:
name="My Filter Name"
enabled="yes"
type="17"
action="Move to folder"
actionValue="imap://name.of.account/Folder/Subfolder"
condition="AND (from,contains,@company.com) AND (from,contains,noreply)"

(No idea what "type='17'" is but all my filters are apparently type 17.)

Anyway I've been using it for years and the current pile of filters does a great job of keeping workspam out of my inbox. Vendor mail, anything from a no-reply address (matched by the example above), etc. goes into one of many file folders (marking as read/unread as desired!), good mail goes into other folders. And any of the folders for workspam also make use of Thunderbird's retention settings: Good mail folders are kept until deleted, workspam folders are cleared automatically, only retaining the most recent X emails or the last Y days of messages, as desired. Clearing out the good folders on occasion is as simple as selecting the old messages and choosing 'Archive' to compress them (but keep them indexed and searchable).
posted by caution live frogs at 11:48 AM on January 28, 2014

PS filters are sequential, so mail that doesn't get matched by filter 1 will be tried against filter 2, until a decision has been made or a "stop filtering" is reached. So you can have one set of filters that tags emails, then a second set that files them based on the tag, etc.
posted by caution live frogs at 11:50 AM on January 28, 2014

And the only downside to Thunderbird is that it won't filter read mail by default. So if you checked mail on your iPhone, you have to select your Inbox and choose "Run filters on folder" upon opening Thunderbird to make sure it catches any mail you read elsewhere while the program was closed.
posted by caution live frogs at 11:52 AM on January 28, 2014