Recently at my real work but not at home, Mail has been hanging for 30 seconds to a minute each time I tried to reply to an email. I would hit the Reply button and have time to make a cup of coffee in the kitchenette before the reply window appeared.

Luckily, the network administrator at the College, Tim Bell, has god-like tcpdump powers. He uncovered what was happening.

Each time I reply to a message, Mail attempts to contact an Apple server through port 80. That’s not a problem at home, but it is at work, where port 80 is blocked and a proxy redirects all HTTP traffic through another port. Mail didn’t respect my proxy settings. It carried on regardless with a process that eventually failed after lengthy delay.

Tim opened the port so that we could see what Mail was trying to do.

Mail was sending the following request based on my .Mac username to certinfo.mac.com (17.250.248.148):

GET /lookup?timgaden HTTP/1.1

In response, it was getting:

The third line in base64 decodes to G\x92\x06\x1777V\xd6W2 (where \x?? means the non-ascii character 92 (in hex), etc.) – so Tim tells me – and the fourth line to acceptance (with a trailing space).

Once we understood the problem, we could google for an answer. It turns out that Jonathan Wight experienced the same thing a year ago. He also provides a fix: delete the ~/Library/Preferences/com.apple.security.plist preferences file.

I’m not suggesting that anything nefarious or underhand is happening here, but it still puzzles me on three fronts.

First, what exactly is it checking and what is the undecipherable response? Is it checking my iChat certificate?

Secondly, why should Mail try to do this when I am replying to a message in my work account on my work server?

Thirdly, why is Mail so stupid? What design oversight makes it overlook my system-wide proxy settings and carry on banging away at port 80, giving me endless delays? Normally, Mail.app helps me to get things done, but not here.

UPDATE: MacGeekery has posted an interesting take on this, which is worth a read.

I hope I made it clear in my post above – although perhaps I didn’t – that I do not think Apple is stealing my credit card information or looking for cracked software or turning my computer into a drone for Apple press releases or doing anything else untoward.

I do think it is puzzling that my proxy settings were ignored and that Mail.app was thus unusable for up to a minute everytime I tried to reply to a message. I do think it is puzzling that the fix was so hard to find. I do think it is fair to expect better of Apple than this.

[Thanks for your help this afternoon, Tim. All my tcpdump are belong to you.]mail.app, apple mail, security, certificates, port 80, reply, hanging, spinning beachball of death, bug, proxySimilar Posts:

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Sven Semmler was delighted with the switch a week ago. He still is; Redmond is still making his day.

In his most recent post he describes how he can still do everything in Entourage that he once did with Mail. He also records some fixes for the problems of double Spotlight results and handling iCal invitations and reminders which users of the new Entourage experience. They would be worth recording, if this site was interested in Entourage.

James Caudill also finds Entourage far superior to Mail.app. He outlines a number of problems that made Mail unusable for him and make Entourage his email client of choice:

Don’t get me wrong. If someone said, “Hey they fixed a lot of stuff in Mail.App and it is stable now.” I will be the first one to try using it again. I love the simple layout and the pretty icons and stuff, but I really need dependability first.

Del.icio.us user mjg is heading back to Entourage too. He says, “Apple Mail just isn’t cutting it, especially with its lack of support for secondary-CA signed certificates.”entourage, mail.app, apple mail, spotlight, syncing, certificates, email, switching Similar Posts:

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This plugin is a front end for gpg and allows you to send and receive encrypted messages. It extends Mail.app’s in-built encryption features in several useful ways.

You can read about the features it offers and its limitation on the GPGMail site.

The new version fixes a compatibility problem with MailTags, needs GPG 1.4 or better, works better in Panther, has a Dutch localisation, works better with AppleScript-generated windows and solves a number of other bugs. (Full changelog ).

The developer warns, “GPGMail is a complete hack, relying on Mail’s private internal API. Use it at your own risks!” But don’t let that put you off.

Get it from the GPGMail web site. encryption, PGP, GPG, plugin, mail.app, apple mail, mailtags, applescript, certificatesSimilar Posts:

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He suggests that,

Encryption seems to lie somewhere between privacy, security, and a mountain of engineering acronyms and standards. Unfortunately for regular people, most of these systems are overbuilt and the process is so painful that I would argue it barely even functions.

He describes his experience of following Joar Winfor’s excellent tutorial on setting up encryption in Apple Mail, drawing attention to the frustrations of the whole process.

He also makes a few suggestions on how some usability could be introduced. A great read.encryption, mail.app, Apple Mail, usability, user friendly, certificates, Thawte, just too bloody difficultSimilar Posts:

• Encryption tutorial for Mail.app
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