Email on Flo's Thoughts

FastMail Configuration Follow-Up

Fri, 13 Feb 2015 19:05:47 +0200

Just a quick update on my FastMail Configuration post: After I wrote that post I ran into some sync issues. Mail.app on OS X had massive problems listing the contents of my folders (and even listing those folders themselves), especially with folders located directly within INBOX.

I had a lengthy conversation with Yassar from the FastMail support team about this issue. We finally figured out that it seems to a bug in Mail.app and he later told me, that they tried to work around this for quite some time. He showed me some posts (1, 2) on their blog regarding similar issues going back as far as 2008.

Long story short: What I ended up doing was moving my INBOX subfolders one level up (so that they now live on the same level INBOX does) and left the rest of the configuration as is. Works for me™.

FastMail Configuration

Sat, 07 Feb 2015 18:57:51 +0200

Yesterday I wrote about my move to FastMail and how smooth that went. I mentioned, that the only caveat was the fact that I had to manually configure the clients to work with FastMail’s IMAP and SMTP servers. This is not as simple as for Google Mail or Yahoo and required me some fine-tuning. So I thought it might be a good idea to share my configuration.

Update: Turns out, there was another issue. I wrote about that one in a separate post.

For me, the configuration seems to differ a bit depending on the device I use. So let’s split split it up into the following two categories.

FastMail on OS X Link to heading

I don’t want to explain the basic setup that has been described on FastMail’s support page again. I just want to mention what I had to change to make it work reliably.

I had some issue with additional directories for sent messages that kept re-appearing on the web interface. This was caused by Mail.app which tried to save sent messages on it’s own. To fix this, uncheck Store sent messages on the server within Mailbox Behaviors on the settings view of your account. Additionally, you need to check Sent Items on SMTP for all your Personalities in Advanced → Personalities. This should fix that.

Drafts, Junk, and Trashed messages are configured to be stored on the server as well. In comparison to the Sent Messages this is only set on the client side.

FastMail on iOS Link to heading

There is an official guide for iOS as well.

I had to manually set all the mailboxes for iOS to use in Advanced to the corresponding server mailboxes.

General Link to heading

You also might want to turn of the notes sync, especially if find additional directories (see Sent Messages) as annoying as I do. FastMail does not support syncing notes anyway.

Also, do not forget to set the IMAP prefix path. This is in the original setup guide, however, I managed to forget about that on one client and this caused some weird listing behavior.

I don’t use the Address Book or Calendar sync (yet). I’m still on iCloud with those services. I will let you know when I moved those services, too.

Hope this helps.

Leaving Gmail

Fri, 06 Feb 2015 11:38:33 +0200

I’ve been meaning to do this as part of my Personal Security Audit project for quite a while now. It’s not that I don’t like Google at all but the power they gathered over the last couple of years with all their services made me feel quite uncomfortable. The same concerns apply to other services like Facebook as well, but that might be a completely different post.

So, first things first. The email server problem. I’d like to report on my experiences I had during that migration and what I ended up with.

Hosting my own server Link to heading

When first thinking about this step I thought it was a good idea do cut loose from any third party email service and host my emails myself. This way, I’d have full control over every little detail of my server and I’d be independent from all the hosters out there. Ars Technica had an excellent four-part how-to on this topic covering everything from the basic system setup to two-factor authentication for your new service.

Naturally, when you take all the control for such an essential service, you also take over all responsibilities. This includes making sure that no one can access your server without permission, your server does not accidentally get blacklisted by other servers (and therefore your messages might get marked spam) and that you keep track of security issues, vulnerabilities and updates on your system.

I did not consider these burdens to be too bad of a trade-off. Until I actually tried it. I set up a server using the above mentioned tutorial and it seemed to be a lovely solution at first. Everything went smoothly and I was able to send and receive my emails with one of my domains. Ultimately, keeping track of all the Ubuntu and package security issues and fixing them on short notice turned out to be more effort than I was willing to commit to.

So this was not for me.

Hosting with yet another third party provider Link to heading

A few of my twitter friends were looking for another email provider around the same time. Namely Winnie and Joggl suggested that FastMail¹ is “the place to go to.” So I thought I should give it a try as well.

First of all, I know that moving to another third party provider was not what I originally intended. Anyway, FastMail has a pretty liberal privacy policy written down in plain English. Also, they do not offer free accounts. This gives me kind of a safer feeling since I don’t feel comfortable being the product.² Besides, I already decided that going all-in on the self-hosting front was not for me. So I came to the conclusion that this might be a fair trade-off.

I signed up for their service and configured the MX records of one of my domains to point to their servers. The configuration went smoothly and I created a few accounts under that domain. The user interface is insanely fast and looks polished. In fact, I found myself using the web interface a few times this week when I could have easily fired up Mail.app.

Only caveat so far is the fact that the configuration on the client side is not as smooth as it is with Google or Yahoo mail accounts. These guys do have their configuration embedded into iOS and OS X while it does not know the least about FastMail’s servers. There does not seem to be any kind of auto discovery service, so the setup needs to be done manually.

Update 2015-02-07: I added a post about my configuration.

After my evaluation was done I decided that I should move my other domains and my main mail account over as well. FastMail offers an IMAP migration service which comes in handy when you want to move older mail accounts. For my main mailbox with ~6 GB it took something like 27 hours to migrate all the mails.

Some of my mails did not appear in my inbox after that migration so I worried that something went wrong. I contacted the support team about this issue and they quickly discovered that there was a problem with one of the timestamps that every message has. They ran a script to fix this and a few minutes later everything was back to normal. I contacted them on a few other occasions and they always replied within a few hours and answered all my questions. Some even in great technical depth.

I’ve been using this setup for about a week now and so far I’m pretty happy I finally made that move. I hope this will serve me this well at least as long as Gmail did.

This is an affiliate link, so if you consider singing up for FastMail as well I would appreciate it if you did it through that link: http://www.fastmail.com/?STKI=13877473 ↩︎
I’m not saying that the old phrase “If its free you’re the product” is generally true, but sometimes I really do feel like it. http://geek-and-poke.com/geekandpoke/2010/12/21/the-free-model.html ↩︎

PGP And S/MIME

Sun, 27 Jul 2014 11:10:07 +0200

I’ve been using S/MIME for quite some time on my university account and on my personal mail account for signing and encryption reasons. I’ve never offered this in public so only few people used this. So, I updated my contact page to include both the information on S/MIME and also my PGP public key. So feel free to encrypt your messages when getting in touch with me.

Ghost Messages in Mail

Thu, 20 Mar 2014 20:00:00 +0200

Apple Mail started to indicate that I’ve got a bunch of draft messages in one of my mailboxes lately. (In my case we’re talking about Google and Exchange accounts.) When I opened the drafts section I expected all those messages to show up but the list remained empty. This bothered me a lot.

Now I finally figured out how to get rid of those ghost messages and it’s rather easy: Just delete the corresponding index file.

In detail:

Quit Mail
Open a Finder window and navigate to ~/Library/Mail/V2/MailData/ (⇧⌘g is your friend if you can’t find your Library directory)
Delete the Envelope Index files (the regular one and the ones with the -shm and the -wal suffixes)
Restart Mail

After that you might have to wait a bit before you can use mail again since it needs to recreate the index, but in my case it was worth the wait.