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Oct 23
2006

Allison Randal

Allison Randal

The Problem of Email

I have a problem, and its name is "email". Many people have the same problem. Not many have it quite as badly as I do. When I say "my inbox is out of control", people respond "Yeah, mine too. I spent 5 hours this weekend and knocked it down from 3,000 messages to 50 messages and I feel so much better." I have over 20,000 messages spread out over 5+ inboxes. This is after I declared defeat 5 months ago, dumped everything into an archive, and started fresh. This is after I unsubscribed from all but the critical mailing lists (Perl lists and internal company mailing lists). This is after spending 3-5 hours every day working on email, and sometimes spending all day on it.


You have to understand, email is the primary means of communication in both my work for O'Reilly and my open source work. When I interview a company and write-up the hot new technology I found, the result and following discussion is email. When I respond to author questions, edit chapters, look for new authors, or develop book proposals it's all via email. When I checkin code or design documents to Parrot, it comes back to me as email. When I review other people's checkins, design proposals, bugs, and feature requests it's all email.

Then there's the semi-personal communications from my bank or credit card company, receipts from online purchases, from my long distance service, from my ISP and colocation accounts. Personal messages are a relatively small percentage of the email I get, and often get buried in the deluge.

Part of it is also spam, though not as much as you might expect. I spend about 30 minutes a day tagging uncaught spam. I spend a half-day (or more) every month or so rescuing falsely tagged spam from the spam folders and deleting the actual spam.

I'm on a quest to eliminate, or at least alleviate, the pain of email. Aside from spam, I can't reduce the flow of email, but with better tools I could be faster and more effective at managing the email I've got.

  • I want spam filtering that works, rather than just skims a few messages off the top. (My O'Reilly account only gets a couple of spam messages a week, so that's my gold standard of spam fighting.)
  • I want accurate complete-text searching across all my inboxes and archives. I want search results that show the context where the search word was found, instead of just the message header.
  • I want tag clouds (or keyword clouds) for each inbox, and keyword lists for each message so I can see categories of other messages related to it. (Using both automatically selected keywords by frequency across my collection of email, and the ability to manually set and block specific keywords.)
  • I want the option of automatically archiving messages older than 30 days.
  • When I flag a message as "Urgent" or "TODO" I don't want it to just change the color of the message subject in my inbox (which gets lost in the sea). I want it to show the TODO messages in a box off to the side of the email window with a quick way to flag them as "done" (perhaps a checkbox).
  • I want virtual views of my email, so I can see, say "all the non-spam messages on all my accounts that arrived in the past hour".
  • I want graphical views of my email, so I can see where the most unread messages are, where the most storage is being absorbed, or where the oldest messages are, and attack that inbox or folder first.
  • I want all this in a client that runs on my laptop without network access so I can work on a plane or train.

I've seen fragments of these features in existing mail servers or clients, or other applications both online and offline, so they're all within the reach of current technology.

I'll be trying out a few solutions in the next few weeks. Let me know if you have any suggestions.


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Bob Monsour   [10.23.06 07:15 PM]

All I can say is that "I want what you want", and I don't have it as bad as you do.

G.   [10.23.06 07:32 PM]

I don't have it as bad as you either. But I understand your points.
I have a "toSpam" adress wich i almost always give when some one - hardly anyone, even rojo.com, ask my mail.
I have two semi-infected adresses. And I try to keep one or two as absolutly non infected. But it is hard to have a usefull mailbox if nobody knows this mail...

Your post reminds a quote Bill Gatesmade few years ago. He described absolutly the same phenomenon.

lhe   [10.23.06 08:30 PM]

Regarding spam: use a spamgourmet.com email address to forward all emails to your real address. if you're afraid spamgourmet-addresses look bad put a forwarding gmail account in front of it.

P   [10.23.06 10:27 PM]

I used to work with a company called Zaplet - like most other companies in the late 90s it was ahead of its time and the VCs wanted some sort of exit route. I still wished they had stuck to the consumer side.

Anyway - I think some of the elments of Zaplet certainly help manage email clutter. The big issue I have is having multiple emails abt the same subject all in different places/times. Gmail and other tools help but they dont do as good a job as Zaplet did (or atleast that was my feeling back then).

Happy conquering your inbox, now i never delete emails. Just move them to an archive folder and let my google desktop search do the magic. Of course even that tool has miles to go....and I'm sure it will.

More than anything I believe some of the web desktops may be able to deliver some of what you are talking abt...or at least hope they do.

Debbie   [10.23.06 11:14 PM]

Finally someone who understands me!!! Nobody I know understands how I can accumulate so much email. I am glad I am not alone. I hope to get what you want too. I once heard about a woman who deletes all of her unread email every Friday afternoon. I want to be that brave, but I am not.

Julian Bond   [10.24.06 12:16 AM]

I'll agree with everything you said and add one more. I want functionality specifically to support mailing lists that makes them look like Usenet with defaults for proper follow-up, quoting, attribution and threading.

I'm using an old mail/newsreader called Turnpike from Demon that I can't get rid of because nothing I've seen does the basics as well. But it's effectively orphaned and is tying me to Windows. But it's got some faults and doesn't do some of the things you're asking for.

And mostly I hate Outlook, Microsoft and the people who use it with a passionate hate. Outlook has done more to help destroy email as a tool than almost anything else I can think of apart from Viruses, Trojans and Spam.

SC   [10.24.06 12:24 AM]

Totally agree...I tried an opensource program called ZOE a few years ago...very nice "hyperlink" user interface...badged as "intertwingling your email!" But at the time it was still a bit beta under the covers. Might be worth another visit?

Simon Cozens   [10.24.06 12:37 AM]

I used to work on a project with these goals and more - not only about helping you manage your email, but in mining the information held in an organisation's email. Various things went wrong, and Google Mail came out and we assumed they'd make it smarter than they did, and so it all fizzled out. For a while I worked on it for fun anyway, because I wanted to use it! Some of the ideas made it out to Email::Store, Buscador, Plucene and a bunch of other CPAN modules.

I think a fair chunk of what you want can be done with Mail.app and MailTags (I don't use it but I know those who swear by it), plus maybe a Gmail account for the searching. But be warned that Gmail doesn't index the content of attachments, which frequently causes me frustration. (Email::Store does)

I'm still convinced that really good email handling is the next killer app. I'd love to have time to head back and pick up some of the ideas again, but there are so many other things to be doing...

dakegra   [10.24.06 01:14 AM]

When I flag a message as "Urgent" or "TODO" I don't want it to just change the color of the message subject in my inbox (which gets lost in the sea). I want it to show the TODO messages in a box off to the side of the email window with a quick way to flag them as "done" (perhaps a checkbox).


Outlook 2003 kinda does this - I've set up search folders for the various colours of flag - red is 'to do', orange is 'waiting response' and so on. Then add the search folders to your favourite folders (right click the folder and 'add to favourite folders') and bingo - you've got a list of the various flagged messages. Rename the search folder to something like 'flag -red [to do]' to keep them all nice and tidy in the list. Click on the folder in the favourite folders and it shows you where the message is. Change the colour of the flag once an item moves from 'to do' to 'waiting', or click the flag and it goes to a tick to show it's done.

Anon   [10.24.06 04:00 AM]

The problem here is not that email tools aren't good enough - they basically are. The problem is that you're subscribed to too many mailing lists. You don't really need all that email, and as proof, I offer this: you haven't read it all, and yet, the world hasn't ended.

Ruthlessly unsubscribe from useless lists. For lists which are are high-volume and only occasionally useful (the skimming problem), set up filters: automatically delete all mail that comes in from this mailing list unless it contains "O'Reilly" or "Allison Randal" or whatever subject you find important. Thus a 200 message/day mailing list gets turned into a 2 message/day list, and both of those messages have a good chance of being useful to you.

The problem is you, not the tools. My email software does almost everything you list as needed, but it's my habits that keep me from being overwhelmed, not the software.

Jason Grant   [10.24.06 04:52 AM]

You will always have these problems with email or any other means of communication.

The reality of the life today is that there is more and more communication happening between people in all formats.

What you can do is to chose to ignore some of it, which will mean that you will be less involved with certain projects.

If you opt for a different format or ask for more ways of 'seeing' things, then all you get is more frameworks and more things to learn about and get used to.

There isn't a simple solution to this (lets all be honest to each other). If you want to work within today's world, all you will need to do (realistically) is: speed up your typing, learn to think faster and make quicker, better and more 'closed' decisions, aim to get things complete as opposed to left open until forever and so on.

Note that these are things related more to the mindset of a person, rather than a technological solution.

That's just my 2 pence.

Thanks,

Jason
www.flexewebs.com

Alex   [10.24.06 06:56 AM]

While we are writing our wishlists, how about some decent built in calendar and sync functions?

Actually, why is there no open source, extendable, application based, Outlook alternative?

Jason   [10.24.06 07:06 AM]

This might sound counterintuitive...but what if you asked for less functionality? For example, when I first started using Gmail, I was frustrated by its apparent lack of features (what do you mean I can't sort my inbox?!), but I eventually got used to the interface -- not to sound Borgian, but I started thinking the way Gmail needed me to think, and not the way MS Outlook wanted me to think -- and now I use it to monitor and maintain several email accounts. It turns out its simplicity masks its sophistication...a combination of rules and labels might just solve your problems. (Except for the tag clouds...though in the Google world of "everything searchable" tag clouds seem unnecessary.) My two cents.

bilogic   [10.24.06 08:11 AM]

I can only partyl agree with these inbox problems. I am subscribed to about 1500 listservers myself. A lot of mailing list still didn't discover the joy to provide RSS feeds instead. I use mail rules to filter my different emails to different mailfolders. This means that my inbox stay practically empty. Spotlight make it able to search for individual emails. Rules kept me out of chaos.

Peter Meyers   [10.24.06 09:25 AM]

Sounds like you need a task/to-do management system more than a specific email client. I was facing a similar problem as yours about a year and a half ago. I picked up David Allen's "Getting Things Done" and haven't looked back. The pit in my stomach of missed emails is gone, as is my bloated in-box. Allen's system is not a panacea, but in my experience it comes pretty close.

Stormdesigns   [10.24.06 09:30 AM]

I think the solution to spam is quite simple, the mail tool needs to have a set allow for familiar email addresses which automatically includes addresses you've sent mail TO. Then it needs to create a list of unfamiliar incoming mail, when unfamiliar incoming mail arrives it sits in one list which can be reviewed at an interval that works for the recipient.

Upon reviewing the list, you can review the mail and or blacklist, whitelist the sender, their domain, their IP address, or a related configurable IP block. Within time, all of your known senders mail would come through, it would be easy to screen new spammers and adding new whitelisted addresses should only require a single click. This suggestion is for Apple, add it to mail or let me know when someone creates a tool that gives mail this feature, K?

Adrian   [10.24.06 09:49 AM]

Stormdesigns: I've been comparing OS X spam filters. I'm going to try Spamfire Pro: http://www.matterform.com/mac_software/spam_email_filter/index.html

Allison Randal   [10.24.06 02:53 PM]

The problem here is not that email tools aren't good enough - they basically are. The problem is that you're subscribed to too many mailing lists.

LOL :) I wish! I'm subscribed to fewer than 10 mailing lists, and those are only the essential lists I need to track for my O'Reilly and open source work. What I didn't mention in my post is that mailing lists are less than half my email traffic.

The problem is you, not the tools. My email software does almost everything you list as needed, but it's my habits that keep me from being overwhelmed, not the software.

I've heard this argument before, but I don't buy it. It's a proven fact that organizational structures that work for 10-person companies don't work for 50-person companies, and the 50-person strategies don't work 500-person companies. I'm sure your strategies work for your volume of email. They don't scale to my volume of mail.

Allison Randal   [10.24.06 03:16 PM]

There isn't a simple solution to this (lets all be honest to each other). If you want to work within today's world, all you will need to do (realistically) is: speed up your typing, learn to think faster and make quicker, better and more 'closed' decisions, aim to get things complete as opposed to left open until forever and so on.

Note that these are things related more to the mindset of a person, rather than a technological solution.

This works to a point, but again, it only scales as far as the human brain. Computers are here to help us. They're better at organizing information than we are, better at performing mundane tasks in a regular way, better at processing data quickly. There's no question that a database is better at storing large quantities of data than my brain is. There's no question that Google is better than randomly surfing URLs hoping to hit a relevant page.


I can't imagine anyone will ever complain that their email client makes it too easy to manage their email. Why not use every technological advantage we can get?

Allison Randal   [10.24.06 03:32 PM]

For lists which are are high-volume and only occasionally useful (the skimming problem), set up filters: automatically delete all mail that comes in from this mailing list unless it contains "O'Reilly" or "Allison Randal" or whatever subject you find important.

You're on to an important point here. The problem is that filters are far too primitive. I can't filter on anything as simple as my name or the name of my company. And I certainly can't delete mail just because it doesn't match a few primitive filters (I might not lose my job, but I'd certainly be doing very poorly at it). What I need is natural language processing. How about a percentage of likelyhood that the message is relevant to me? It takes me time to skim through a message to see if it's relevant. But, if I could train my email client in keywords to watch, and keywords to rank down, then I could flick open a message, check the keyword list and percentage of relevance, read the first couple of sentences if I'm feeling particularly thorough, and delete it.

Computers are, so far, pretty poor at making decisions for me, but they're really good at summarizing the information I need to make the decision.

MikeC   [10.24.06 03:56 PM]

"Actually, why is there no open source, extendable, application based, Outlook alternative?"

There are several. Evolution is the first to spring to mind.

Alex vdG   [10.24.06 05:42 PM]

I think there is a different way to solve this and it involves a well thought out multiple address approach. Gmail , Yahoo, Earthlink are all beggning to grapple with the idea of having multiple email addresses at your disposal. They are not quite there yet - I use Reflexion (www.reflexion.com) which allows me to create an unlimited number or dynamic email addresses that are (this is key) managed by the server.

In your case you could use unique addresses for your different mailing lists as a way to keep them sorted, and spam free (for example joe.parrot@abc.com , joe.forum1@abc.com and so on) - the cool thing about these guys is that they allow me to decide whether that address is open to the world, not shared (i.e one domain or sender only, or filtered) - lots of power.

No tagging unfortunatley - but I think they are looking at that problem

Alex vdG   [10.24.06 05:43 PM]

I think there is a different way to solve this and it involves a well thought out multiple address approach. Gmail , Yahoo, Earthlink are all beggning to grapple with the idea of having multiple email addresses at your disposal. They are not quite there yet - I use Reflexion (www.reflexion.net) which allows me to create an unlimited number or dynamic email addresses that are (this is key) managed by the server.

In your case you could use unique addresses for your different mailing lists as a way to keep them sorted, and spam free (for example joe.parrot@abc.com , joe.forum1@abc.com and so on) - the cool thing about these guys is that they allow me to decide whether that address is open to the world, not shared (i.e one domain or sender only, or filtered) - lots of power.

No tagging unfortunatley - but I think they are looking at that problem

Roger Purves   [10.24.06 10:21 PM]

There are lot of posts here preceding this one. I can read them all without "opening" any of them. I only have to scroll. I want an
email program to provide this kind of view of big chunks
(100 messages at a time, say) of my email. And, in the
same view, I want a delete button displayed beside every
message. Then I could thin messages quickly; something
I can't do now.

NatC   [10.25.06 01:17 AM]

Could be worth looking for private wikis (with some tweaks, and RSS feeds for notification of changes) as an alternative to email. No spam. No sorting out. No archival headaches. Search. Continuous conversations. Seems to match your needs for part of your work at O'Reilly.

Matthew Cornell   [10.25.06 08:02 AM]

I think there are two distinct problems. First, your volume is very high, so reducing it makes sense. Getting off lists, moving as much as possible to RSS, etc.

Second, you need need to be extremely efficient at *processing* your email, something I didn't see mentioned above. The one I use is David Allen's "Getting Things Done" methodology (AKA GTD), which is a system to handle all stuff in a person's life, including email. (I also coach people in it.) Note that processing does not involve doing (unless

Juliana Aldous Atkinson   [10.25.06 09:09 AM]

I'm sure many of these features will be a reality in the future. In the meantime, I'd recommend two books, Take Back Your Life by Sally McGhee (caveat that my team published it), and Never Check Email in the Morning by Julie Morgenstern. I'll post more on my blog.

Jack Sinclair   [10.25.06 10:40 AM]

Two suggestions:

1) I have seen the GTD suggestion and I can't recommend it enough. I have used it for over three years now and certainly deals with a lot of your issues. We even teach it in my Company.
2) Outlook 2007. Probably not a great suggestion given it is still in Beta but it does a good job with category clouds and other features you are looking for and actually has a pretty effective local spam filter. We use Postini in my Company on the server side and combined with my Outlook catches most of my spam.

Good luck

-- Morgan Schweers, CyberFOX!   [10.25.06 11:26 AM]

Greetings,

But, if I could train my email client in keywords to watch, and keywords to rank down, then I could flick open a message, check the keyword list and percentage of relevance, read the first couple of sentences if I'm feeling particularly thorough, and delete it.

You want a scoring, threaded mail reader. Scoring has been VASTLY underrated as a method for organizing information. The few scoring Usenet readers mostly died with shell-based access to Usenet, although Gravity and a few others managed to include the ideas.

I sincerely doubt this would be hard to do. I can think of a procmail script to do it, for example. All you need is for your existing email reader to be able to provide 'sort by custom column', and a few pre-processing rules (to add or subtract from an 'X-Score' header), and you're 90% there.

You don't need NLP for this. (As someone who's dabbling in NLP currently, I'm pretty positive of that.) You could use the same technique that Spam filters use, except in reverse. Bayesian classification using 'interestingness' as the classifier. You would mark items as 'Interesting', or 'Uninteresting', and it extracts the tokens (words) from the mail, and trains on it.

You wouldn't use it as a filter like you use Bayesian spam filtering, but as a sort option, where items that best match your 'interesting' classifier filter up.

There are excruciatingly simple Bayes-based classifiers in Python (Reverend) and Ruby (Bishop), and I'm sure you can find them for other languages. I've played with Bishop, and it's very solid and fascinatingly useful.

Just a thought; hope it helps... If you build something off of it, let me know!

joh   [10.26.06 12:11 PM]

Just one point: Archiving old mail tries to solve the problem from the wrong end. A mail client should by default only display mail that is either unread or flagged as "to be dealt with later". Mail you've read (or marked as read) and not flagged, has to disappear without visible trace. This way you just have to work through your mailboxes and they will be cleaned up as you do your stuff.

Allison Randal   [10.26.06 03:46 PM]

A mail client should by default only display mail that is either unread or flagged as "to be dealt with later". Mail you've read (or marked as read) and not flagged, has to disappear without visible trace.

Hmmm... I like the idea. The one thing I'm not sure about is that I'd want it to prompt me before automatically removing a read message (the simple process of loading new email, or deleting a message often brings a message into focus and marks it "read" even though I'm not reading it). With all the prompts, I'm not sure if my efficiency at processing email would go up or down.

Allison Randal   [10.26.06 04:08 PM]

You don't need NLP for this. (As someone who's dabbling in NLP currently, I'm pretty positive of that.)

As a linguist, I'm positive I do need it. There's some incredibly cool work being done in this space. (Take a look at IBM's UIMA.) These sorts of advanced features are coming. They just haven't worked their way down to the level of mass-market email clients yet.

You could use the same technique that Spam filters use, except in reverse. Bayesian classification using 'interestingness' as the classifier. You would mark items as 'Interesting', or 'Uninteresting', and it extracts the tokens (words) from the mail, and trains on it.

Bayesian classification is NLP. And yes, this would be a nice feature in an email client. Not a total solution, but a nice addition.

Nicholas Clark   [10.27.06 06:43 AM]

I spend about 30 minutes a day tagging uncaught spam.

You comment that less than 50% of your e-mail is list mail, which to me implies that the bulk is e-mail that you're explicitly put in the To: or Cc: header of e-mail, and need to determine if you really needed to be there. (The bane of e-mail - it becomes trivial to externalise the cost of deciding who needs to receive information, by simply carpet bombing everyone who might.) You say you don't think that existing solutions will help with filtering your e-mail, which I infer would be this task of deciding which messages you need to react to. Hence it appears that the only thing to optimise is the time spent dealing with spam, which is currently 2% of your day. Can you get better spam filtering?

Scott Lawton   [10.28.06 12:56 PM]

30 min/day on spam? Wow. Try SpamStopsHere. For me, it was a HUGE improvement over SpamAssassin and such. (The usual disclaimer: I'm just a satisfied customer.)

Erik Hetzner   [10.30.06 05:47 PM]

Here's my suggestions. I don't deal with nearly as much email, but I think it's an important problem. I truly don't think you can fully solve this problem with the software that exists today.

General suggestions. It's been my experience that email users spend a long time waiting...waiting for that message to be moved, deleted, purged, fetched, etc. This is boring. It becomes intolerable at very large email volumes. Too many clients are incapable of handling large sets of email.

  • Move away from mbox; it's slow. Try maildir. Use a dedicated imap server for yourself. I like dovecot.

  • Tips for imap: don't move email to the trash, flag it as deleted. This is faster.
  • Use a client that queues up your deletes, queues up your message moving, etc. This saves a lot of time.
  • Use a terminal mail reader. Graphical readers are just too slow. Also, you waste much time with all that mouse maneuvering. Preferably, use one for Emacs. Preferably Wanderlust, which handles imap properly.

More specifically, I really do think you should try a setup of the following:

Put all your mail in maildirs on a server. Use dovecot as an imap server against this.

Use the Wanderlust email client for Emacs.

How will this help you?

I want spam filtering that works, rather than just skims a few messages off the top. (My O'Reilly account only gets a couple of spam messages a week, so that's my gold standard of spam fighting.)

Not sure about spam; spamassassin seems to work for me. So did bogofilter, though. There are many solutions, and there are definitely ones that work.

I want accurate complete-text searching across all my inboxes and archives. I want search results that show the context where the search word was found, instead of just the message header.

I haven't found anything that does this totally right, yet. Beagle on linux seems pretty good, but not perfect. Indexing mail is pretty easy; I've got 50 lines of Ruby that indexes with Ferret against imap email boxes. The trick is integration with a client. This is easier if you use a scriptable client, of course. Like Wanderlust. Wanderlust supports a full text indexer called namazu, but I've never used it.

I want tag clouds (or keyword clouds) for each inbox, and keyword lists for each message so I can see categories of other messages related to it. (Using both automatically selected keywords by frequency across my collection of email, and the ability to manually set and block specific keywords.)

Imap has the ability to support arbitrary flags against messages. Flags are tags. Dovecot supports adding arbitrary flags to messages. Very few email clients do. Thunderbird doesn't. Wanderlust does. You can then filter by flag in folders or across all your messages.

I want the option of automatically archiving messages older than 30 days.

Wanderlust does this. Don't other clients do this nowadays?

When I flag a message as "Urgent" or "TODO" I don't want it to just change the color of the message subject in my inbox (which gets lost in the sea). I want it to show the TODO messages in a box off to the side of the email window with a quick way to flag them as "done" (perhaps a checkbox).

See above.

I want virtual views of my email, so I can see, say "all the non-spam messages on all my accounts that arrived in the past hour".

This is pretty close: http://www.gohome.org/wl/doc/wl_39.html; you can't specify by the hour, but that is probably easily changed.

I want graphical views of my email, so I can see where the most unread messages are, where the most storage is being absorbed, or where the oldest messages are, and attack that inbox or folder first.

I don't know about this.

I want all this in a client that runs on my laptop without network access so I can work on a plane or train.

This is what imap disconnected operation is for. Unfortunately, the only clients I know what handle it properly are Thunderbird and Wanderlust

I'm looking forward to seeing what you come up with. I definitely stand by what I've said about terminal clients, and especially Wanderlust.

Martin   [11.16.06 02:00 AM]

Hi Allison,

Just some thoughts...

I don't know if you use a Mac, but if you do...

In Mail.app, you can have every mail that comes in be subjected to rules. Each rule contains the possibility of triggering an AppleScript. This can provide you with the extra uumph! you need in order to manage your mail.

For example, each list's day's mails could be converted into a web page, which you can then scroll through much faster than reading each mail itself (assuming that you are reading each message, rather than subscribing to the digest). In effect, you are making your own digest, but you can build the web 'digest' page so that you can click on the message sender and reply to them/the list.

The notion of the to-do could also be AppleScripted. (Note: AppleScript can call other scripting languages via the Terminal, so you're not tasked with learning AppleScript).

I already have a rule which will archive my mail after 93 days. It requires that I select all messages and run the script, but it works for what I need. A more sophisticated ruleset could parse the messages and archive to a particular folder, etc. With iCal scripted, it could trigger 'run mail', 'convert list to webpage', 'archive xyz', etc.

Now, using Mailsmith by BBEdit should enhance this functionality, as it's based on the BBEdit text engine, so it has real search functionality. I don't and never have used it, but sometimes I feel that I should.


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