Messaging

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Funambol, formerly Sync4j, is claiming that its latest product, Funambol 3, could function as an open-source Blackberry workaround, allowing push e-mail to be delivered to a variety of mobile devices, including Blackberries.  This is particularly important in light of the threat of a Blackberry shutdown due to the RIM-NTP patent dispute.

Currently in beta, the v3 server software runs on Linux or Windows, and clients are available for Outlook, Windows Mobile, Blackberry, Palm, and (believe it or not) iPod.

More information can be found in this article.

Some people are also suggesting the use of open standards to ease the impact of a potential Blackberry shutdown as well.  While not as functionally rich as a typical Blackberry implementation, the use of POP3/IMAP4 and SMTP to handle mobile messaging needs is certainly very viable.  This is easily implemented via most commercial messaging systems and through a number of open source packages as well.  For example, I use Dovecot and Postfix to provide IMAP4/SMTP support for my Treo, all secured by SSL/TLS encryption.  Like the Funambol approach, this also offers a great deal of client-side variety as well, instead of locking users into a single client device.

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Badmail and Exchange 2003

If you are planning an in-place upgrade of your server running Exchange 2000 to Exchange Server 2003, beware of the Badmail folder.  Apparently, during the Exchange Server 2003 setup process, the setup application tries to go back and stamp ACLs (access control lists) on all the objects in the installation directory.  This, by default, includes the Badmail directory.  If your Badmail directory contains lots of items (which, in an Exchange 2000 installation, it probably does), then this can cause the Setup process to appear to be hung.  Microsoft has published this KB article discussing the issue and the resolution.

Fortunately, in Exchange Server 2003 SP1, Microsoft has changed the behavior of Exchange to use the Badmail folder only if explicitly configured to do so (see this KB article).  No more monitoring the Badmail folder!

In addition, for those networks that have not yet deployed Exchange Server 2003 SP1, Microsoft has released the BadMailAdmin tool.  I’ve tested this, and it works as advertised.

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I blogged earlier about my frustration with the Mac OS X Mail.app mail client and its apparent lack of STARTTLS support with IMAP4.  Well, on a whim today I decided to take this issue back up again.

Since Microsoft Exchange does not support STARTTLS, I had to use Perdition as an IMAP proxy in front of Exchange.  Earlier attempts to get Mail.app to do STARTTLS had failed (not sure why), but today I decided to try changing the IMAP port from 993 (the default when you check the “Use SSL” box) to 143 (the standard IMAP4 port).  Oddly enough, it seemed to work!

Curious to find out for sure, I trotted out tcpdump on the mail gateway running Perdition to capture traffic to/from Mail.app and to/from the back end mail server.  The traffic to/from the back end mail server was transmitted in the clear (I used plain text messages so that I could see the content), but the traffic to/from Mail.app was not readable.  I also saw Mail.app issue a CAPABILITY command, then issue a STARTTLS command.  Bingo!

So, it appears that Mail.app does indeed support STARTTLS for IMAP, but only if you set the port number back to 143 after checking the “Use SSL” checkbox.

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Split E-Mail Routing

Now that I have Perdition up and running (although not in the way I really wanted; see my post titled “Perdition Working Now”), I’m moving on to setting up an internal news server.

Before I can get the internal news server up and running, though, I must first address the issue of e-mail submissions to these newsgroups. See, right now I can send an e-mail to [email protected] (this is obviously an invalid address) and that message will be posted to the newsgroup. This works well because the mailboxes and the newsgroups live on the same server and the mail gateway can route all messages to this server.

If I setup a separate news server, however, I’ll need some e-mail addresses to be directed to the mail server, but other e-mail addresses (the e-mail addresses for the newsgroups) to a different server altogether. I think that Postfix can do this, but I don’t know that for certain yet. I suspect that the answer lies somewhere in the mystery of virtual_alias_maps, but I just can’t wrap my head around it right now. Of course, it is getting late here so that may explain it.

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Perdition Working Now

I finally managed to get Perdition working.  Still unable to confirm if Mac OS X’s Mail.app supports STARTTLS (my experience thus far says No), I had to resort to using Stunnel to wrap IMAP inside an SSL tunnel, then forward the IMAP traffic to Perdition on the same host.  The Perdition proxy then passes the traffic to the back-end mail server.  It’s not the solution that I really wanted, but it will do for now.  At least the Exchange Server 2003 IMAP server isn’t exposed directly to external networks.

On a slightly related note, the Slipstick Systems web site has a link to an IMAP proxy server that implements STARTTLS as a workaround for Exchange’s lack of native support for STARTTLS.  The IMAP proxy can be found at http://www.slipstick.com/files/imapproxysvc.zip.  So, if you have an IMAP4 client that supports STARTTLS and want to connect it to Exchange, you can use this IMAP proxy.  At least, until Microsoft puts STARTTLS support into Exchange directly.

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In my experiments with Perdition, I learned a couple of very interesting facts. First, the IMAP4 implementation on Exchange Server 2003 does not support the STARTTLS command, as described in RFC 2595 and re-affirmed in RFC 3501. Instead, Exchange expects an SSL session to be established immediately, and then IMAP is spoken. This is similar to the “smtpd_tls_wrappermode” directive that Postfix supports.

Second, it appears that the Mac OS X Mail application (commonly referred to as Mail.app) also uses this IMAP-over-SSL approach, since I’ve been using Mail.app to connect to Exchange using IMAP with SSL for quite some time. I’m trying to confirm that now, but having precious little luck finding any definitive information one way or the other. If anyone knows for certain, please let me know. I’m going to keep searching.

This is one of those things that just makes me crazy.

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Miscellaneous Projects

In my copious spare time (fellow parents out there know this is a joke), I’m working on a couple of miscellaneous technical projects:

Internal news server:  I’m having so many problems with NNTP-based access from Unison to Exchange Server 2003 that I’ve decided to setup an internal NNTP server using Linux and INNd.  Linux I’m familiar with; INNd is completely new to me.  Wish me luck.

IMAP proxy:  This would use Perdition to proxy IMAP4S requests to my mail server.  I’ll probably have Perdition handle IMAP4S and then pass IMAP to the back-end server, offloading the SSL work to the proxy.

Squid log analysis:  I’m looking for a way to parse down the logs from my Squid web cache.  Once I find a way to do this, then I can really begin offering Squid and SquidGuard as a content filtering solution to some of my customers.

I’m sure this stuff is probably old hat to some of you out there.  Feel free to contribute some helpful information or URLs. I’ll keep you posted on how things proceed with these and other projects as they develop.

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