View Source: MuttFastmailMailappMac

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!!! How to Use Mutt, ~FastMail, and Mail.app Together on Your Mac

by Philip J. Hollenback %%%
Originally [published in MacDevCenter on January 18, 2005|http://www.macdevcenter.com/pub/a/mac/2005/01/18/fastmail.html].

In many ways, the Mac is the best of two worlds. On the one hand, you
have all the beautiful GUI-based programs that the Mac has always been
famous for. On the other, Mac OS X is at its heart a Unix OS, so all
the command-line tools are available as well. The result is an
incredibly powerful and flexible platform.

Like a growing number of users, I came to the Mac via Linux. I have
been using various Linux distributions as my pr imary desktop for
years. When it came time to get a laptop, I decided it was time to
look at a Mac, because frankly I was tired of dealing with all the
hardware issues Linux laptop users face (modems that don't work,
unsupported wireless cards, and so on). The real question, however,
was this: would I be able to combine my command-line environment with
the graphical tools available on Mac OS X? The answer is yes, and in
this article I describe one part of that integration: email.

!! The Tools

For years I have run my own mail server and managed my own
mail. That's the mark of a real sysadmin, right? I won't deny it's a
good learning experience, but I did get tired of dealing with things
like spam, system upgrades, and backups. I just wanted to read my
mail.

Coincidentally, I was notified that the service I used to host my
personal server was going away. Thus, it was the perfect time to shop
around for a new email solution.

I knew I wanted both a sophisticated web interface (for when I'm on
the road) and access via the command line (for when I'm at home). On a
friend's recommendation, I tried [FastMail|http://fastmail.fm] and was
quickly hooked. ~FastMail offers a very powerful web interface, and you
can also access your email with IMAP. That meant I could use any mail
program that understands IMAP - which is pretty much any mail program
these days.

The obvious program to use was Apple's own Mail.app. While earlier
versions of Mail.app were pretty rough around the edges and lacking in
features, the current version is robust and powerful. Plus, I knew
that it would take advantage of all the Mac niceties like easy image
and HTML mail handling.

But what about the command line? There was no way a Linux diehard like
myself was going to give that up. I've been using the premier
power-user mail program [mutt|http://www.mutt.org] for years. I did a
little research and found that mutt ran on Mac OS X and could be
easily installed via [Fink|http://fink.sf.net]. mutt supports IMAP as
well, so I could see my tools were coming together.

!! Installation

Mail.app was already installed on my Mac, and setting up ~FastMail was
as simple as signing up on the web site. I opted for a paid account so
I could save more mail on the server. My plan was to move all my
existing mailboxes to ~FastMail, which would require about 50MB of
space. (The free ~FastMail account gives you only 16MB.) For a
reasonable $25 per year, I got 600MB of storage on ~FastMail, as well
as some other useful features such as ~SpamAssassin filtering. That was
to prove very useful.

Installing mutt was a bit more work. First I had to install Fink, the
free software manager for Mac OS. Fink works with the Debian package
manager apt to provide easy installation of all the standard free
software from the Linux world. Installing Fink was simple: I just
downloaded the [Fink binary installer|http://fink.sf.net] and ran
it. Make sure to follow the documentation after doing this, because
setting up your environment correctly requires that you do some
work. After this, installing mutt was a simple matter of running
apt-get in a terminal window:

<pre>
$ sudo apt-get update
</pre>

(to get the latest package list) and

<pre>
$ sudo apt-get install mutt
</pre>

To install mutt, I knew I would need a few helpers, so I also
installed aspell, urlview, lynx, and unzip using apt-get as well.

!! Configuration

! Mail.app

As usual, configuring the tools is the most time-consuming part of the
process. Luckily, I documented the steps I had to take and can pass
the savings on to you.

To configure Mail.app, go to the =Mail->Preferences= menu and click on
the Accounts tab. Then, click on the plus sign to create a new
account. Change the settings as follows:

[http://www.hollenback.net/writings/mail.app_account_setup.jpg]

You have to now find a way to send mail out from your system. While
it's technically possible to send mail directly from your Mac, it's
generally better to relay it through a server. If you have paid for an
upgraded ~FastMail account, you can use its SMTP server
[as detailed here|http://www.fastmail.fm/docs/faqparts/ExternalMail.htm#ServerDetails].

Alternately, if you have a .mac account, you can use that SMTP
server. Finally, as a fallback, you can run a mail server on your
Mac. Just be aware that this may result in problems - your mail will
look much more like spam, and some consumer broadband networks block
port 25.

I use [Pobox.com|http://www.pobox.com] for mail forwarding, and it
provides a free SMTP server too. Many mail services provide an SMTP
server, so you should be able to find something. Also, consider using
SSL if your server supports it. That way, Mail.app communicates with
the outgoing mail server over an encrypted channel. That probably
isn't terribly important, as once your mail gets to that server, it
will be unencrypted for the rest of its journey anyway.

[http://www.hollenback.net/writings/mail.app_smtp_server_setup.jpg]

Once you have the account basics set up, move to the Special Mailboxes
tab. Select all the check boxes on this screen to ensure that Mail.app
places all its special mailboxes such as Sent and Trash on the server
and doesn't store them on the local system.

[http://www.hollenback.net/writings/mail.app_special_mailboxes_setup.jpg]

Under the =Advanced= tab, select "Automatically synchronize changed
mailboxes" and use the IMAP path prefix =INBOX=. You will use password
authentication for that, and you can turn on SSL if you wish. That
will encrypt the communications between the IMAP server and Mail.app.

[http://www.hollenback.net/writings/mail.app_advanced_setup.jpg]

Note that Mail.app and ~FastMail use slightly different naming
conventions for some folders. Mail.app saves copies of sent messages
to Sent, while ~FastMail uses Sent Items. The easiest way to fix this
is to tell Mail.app to use the ~FastMail folders. In Mail.app, select
each folder on the server you wish to use, and go to the =Mailbox->Use This Mailbox For= menu. For example, select Sent Items on the
~FastMail server and Use This Mailbox For Sent. Here is the list of
folders on each system:

Mail.app folder |
  ~FastMail folder
Trash |
  Trash
Sent |
  Sent Items
Drafts |
  Drafts
Junk |
  Junk Mail

That is all you should need to do to set up Mail.app to access your
~FastMail account. Test by launching Mail.app and verify that you can
send and receive mail.

! Mutt

It is possible to open IMAP folders in mutt without doing any further
configuration. To test this, run mutt in a terminal window and press
=c= to open a mailbox. Enter your Fastmail.fm mailbox in
this format:

<pre>
imap://mail.messagingengine.com/
</pre>

When prompted, enter your ~FastMail username and password. While this
is good for initial testing, it would be quite cumbersome to do this
every time you wanted to change mailboxes. The solution is to place
your IMAP server settings in the mutt configuration file
=$HOME/.muttrc=. If you don't have this file, create it. Add the
following entries:

<pre>
set imap_user=<your fastmail user>
set imap_pass=<your fastmail password>
set record=+"Sent Items"
set postponed=+Drafts
set imap_home_namespace="INBOX"
set folder="imap://mail.messagingengine.com/INBOX"
set spoolfile="imap://mail.messagingengine.com/INBOX"
set mask="."
</pre>

Mutt will now go directly to your ~FastMail account on startup and
won't ever ask for a username or password. This will also save a copy
of all your sent and postponed messages on the server. This matches
the settings in Mail.app (assuming you followed my instructions above)
and in the ~FastMail web interface. This means that you can start
editing a message in ~FastMail, save a draft, and then open it in
Mail.app or mutt with no problems.

!! It's Working - Now What?

You are now set up to receive mail using all three
applications. However, you probably can't send mail using mutt
yet. The reason is that mutt, unlike many other mail programs, does
not come with an integrated facility to send mail. Instead, it relies
on your system mailer (sendmail). That works fine on traditional Unix
systems. However, desktop computers are usually not configured with
sendmail to send mail directly.

You have two choices here. The first is to configure a full mail
transfer agent (MTA) such as sendmail or postfix. This is usually
overkill for a desktop system because it also sets up your system to
receive mail, which you probably don't need (or want). A
lighter-weight alternative is a send-only sendmail replacement such as
sSMTP or esmtp. I recommend esmtp because it supports SMTP
authentication. You will need authentication with most SMTP servers
(~FastMail requires it). esmtp is currently not available via Fink, so
you will need to build it from source. You can download the source
from the [esmtp sourceforge site|http://esmtp.sourceforge.net]. After
you install the esmtp program, create the configuration file
_$HOME/.esmtprc_ containing the following (assuming you will be using
the ~FastMail SMTP server):

<pre>
hostname = mail.messagingengine.com
username = <your fastmail username>
password = <your fastmail password>
</pre>

And add the following to your .muttrc:

<pre>
set sendmail=/usr/local/bin/esmtp
</pre>

Now mutt will hand outgoing messages off to esmtp. esmtp will then
authenticate with the ~FastMail SMTP server and relay the message.

!! But What About My Address Book?

This is the one place where everything falls apart,
unfortunately. There is currently no way to synchronize the address
books between all three applications. The best you can do is access
your Apple address book in mutt. To do this, download and install
[contacts|http://gnufoo.org/contacts/] (a command-line interface to
the Apple address book). Then add the following to your .muttrc:

<pre>
set query_command="contact -l -f%e %s"
</pre>

Then press =Ctrl-T= to complete addresses from your Mac address
book. Note that this is not a perfect solution, as it doesn't return
results in exactly the format mutt expects. The fix for this would be
to create a wrapper script to adjust the results. However, it's a
perfectly usable mechanism.

Another alternative would be to run a regular cron job that uses
contacts to build your mutt address book out of the Mac address book
every night. The downside of that approach is you have to remember to
never save addresses in mutt (because they will be overwritten the
next time the cron job runs).

At this time, there is no way to synchronize addresses between
~FastMail and any other mail system. Hopefully the folks at ~FastMail
will address this in the near future.

!! Further Mutt Improvements

One thing mutt lacks in comparison with other mail programs is IMAP
header caching. Every time mutt needs to know something about a
message on a remote system, it has to request the header again. This
slows mutt down considerably (although in practice it isn't a
showstopper).

A solution can be found in the [unofficial mutt imap header caching patches|http://wwwcip.informatik.uni-erlangen.de/~sithglan/mutt/]. I
have not tried these patches yet, but they seem well-supported as
evidenced by the number of vendors who ship mutt with these patches
preinstalled.

Another mutt improvement would be to use SSL to encrypt communication
with the IMAP server. In practice, this is not a huge concern because
email is not particularly secure to begin with. However, if you are
concerned about this, you should rebuild mutt from source and enable
this feature. (The version in Fink has SSL turned off, probably to
avoid legal problems.) This seems a worthwhile avenue to explore,
especially since the ~FastMail IMAP server supports SSL. Once you do
that, it probably also makes sense to build a version of esmtp that
supports SSL as well so you can encrypt all mail to and from your mail
server.

!! Final Thoughts

IMAP is a mature and robust protocol. The power of IMAP is that it
acts as a generic mail transport and synchronization mechanism. As
I've demonstrated in this article, you can easily set up three
different mail applications to access a common mail store using
IMAP. This gives you the flexibility to switch between applications as
needed (or desired). Need to process and respond to a lot of text
messages quickly? Use mutt. Need to deal with lots of graphics or
HTML-formatted mail? Use Mail.app. On the road? Access your mail with
the ~FastMail web interface. No matter what mechanism you use, your
messages remain in one location.
View Source: MuttFastmailMailappMac

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