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Alpine on Mac OS X

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Notes on building and running alpine under Mac OS X.

Paul Heinlein
First published on February 4, 2005
Last updated on September 22, 2020

Several years ago, my main workstation at work became a PowerBook G4running Mac OS X. I tried using the included Mail.app, but I missed theflexibility of Pine, my favorite mail client. So I set to compiling andinstalling it on my laptop. It wasn’t initially obvious how to workaround the Mac-isms, but so far I’ve been able to get most things towork as well as they do on my Linux boxes.

Since then, I’ve migrated from Pine to Alpine, its successor. At leastone Pine developer has said that it’s not too much of a stretch to saythat Alpine 1.0 could be considered Pine 5.0. In a standard terminalwindow, Alpine looks and acts pretty much like Pine, but under the hoodthere have been some substantial code revisions. Among other things,Alpine works and plays pretty well with UTF-8 (aka Unicode) charactersand typefaces. Also, the license has been altered, making it likely thatpeople will be able to distribute patched binary versions ofAlpine—something not permitted under Pine’s license.

I should note that I don’t store any mail locally; my inboxes andfolders are all on remote IMAP hosts. I assume that a local mail storeon a Mac will work as expected, but I don’t have any experience with it.

Pine had a idiosyncratic build process, but with Alpine the UWdevelopment team began to use the GNU autoconf system. The migrationisn’t complete—too many legacy operating environments supported by thec-client code can’t use it—but the developers have hinted strongly thatthey’ll be dropping support for many older environments in the nearfuture. The upshot is that while Alpine builds using the standardconfigure script, there’s still several old Pine build scripts underthe hood.

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To build Alpine on OS X, you’ll need to install the Xcodepackage. My hunch is thatanyone interested in using a command-line mail client on the Mac hasalready done that, but stranger things have happened.

The latest versions of Alpine require OpenSSL version 1.0.0c orhigher. macOS 10.13 ships with LibreSSL, so I chose to link Alpineagainst a third-party OpenSSL installation. I useMacPorts, but a lot of people useHomebrew. The script below assumes a MacPortsversion of OpenSSL, but it’d be easy to modify for Homebrew.

If you’re connecting to your mail server using a secure SSL or TLSsession, you will likely encounter Alpine’s dreaded SSL/TLS CertificateValidation Failure warning:

You will see this message even if your server has a certificate signedby a well known Certificate Authority (CA) like VeriSign or Thawte.

Since this version of Alpine is linked against a non-system OpenSSLinstallation, you’ll have to figure out where it keeps its storeof recognized CAs. For MacPorts, the file is off in /opt/local:

  • /opt/local/share/curl/curl-ca-bundle.crt

You’ll need to add the certificate(s) you want to that file manually:

Then relaunch Alpine.

I’ve tried running Alpine both in the standard Terminal utility and inthe xterm provided by X11 for Mac OS X (aka XDarwin). It works ineither environment, but I prefer the Terminal because it’s got bettercut-and-paste support and it seems to handle character-set issuesbetter.

I use a larger font for mail than I do for regular Terminal sessions.For me, 12 or 13 pt. Monaco works well, and it looks even better withanti-aliasing turned on.

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You can verify the antialiasing check box by navigating toTerminal -> Preferecnes… -> Profiles -> «name of profile» -> Text

The Terminal application has several different profile, eachwith its own colors and fonts. You’ll need to repeat the previouscheck for each different profile.

Mac OS X makes it easy to launch helper applications for viewing URLsembedded in messages or attached files like images, PDF files, MS Worddocs, or whatever. The secret lies in the open utility, which knowsall about which applications you prefer for which MIME types.

Opening URLs with your default browser

Two settings need to be tweaked if you want to be able to view URLsembedded in messages sent to you. First, you need to enableenable-msg-view-urls option. Second, tell the url-viewers optionabout open:

Note that the quotation marks are necessary to preserve the whitespace.

That’s it! If someone sends you something with some text that evenvaguely resembles a URL, it’ll appear in bold within your Terminal. Usethe up or down arrows to highlight it, then press the Enter key. Yourdefault web browser will appear and begin loading the page.

Opening URLs with a different browser

I’ve gotten to the point that I prefer opening URLs embedded in e-mail messageswith Google Chrome in incognito mode rather than with my default browser, whichhappens to be Safari.

I was unable to configure this change completely in my .pinerc file, so Iended up writing a wrapper script and referencing that script in my alpine configuration.

The script itself is pretty simple. See the open(1) man page for details.

I installed that script as /usr/local/bin/url-viewer and then pointed alpine that way:

Opening attachments

Alpine relies on the system mailcap to associate any given MIME typewith the application used to execute it. The Darwin build Alpine doesn’tinclude a default search path for mailcap, and OS X doesn’t include oneanyway. Overcoming all this is pretty simple.

Modify .pinerc so that it knows how to find your mailcap:

Create a simple ~/.mailcap file that essentially relies on open andLaunchServices for all its MIME savvy:

I also like to open HTML attachments with incognito Chrome. If you’d liketo do the same, just add this line to the top of your mailcap file:

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That does it. Alpine is now able to launch attachments without anytrouble.

Wisely, Apple’s software developers tied command-line printing intothe larger print system, so lpr and its ilk work as expected.Printing from Alpine is therefore just a matter of getting theoutput formatted according to your tastes and piped off the lpr.Personally, I like the e-mail formatting provided by enscript,which formerly was included with Darwin but is now available viaMacPorts.

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The one potential pitfall of this recipe is that it will only sendoutput to your default printer. If you want to send mail to a differentprinter, then you’ll have to change your default printer before printingfrom Alpine, or you’ll have to set up a separate definition for eachpotential printer using enscript’s -P option.