We have many Palm phones running Palm OS, in particular we have a lot of Palm Centros although we have some other models as well (but they all run Palm OS, not Windows Mobile). We’ve had GoDaddy SSL certificates for a while for our Exchange 2003 server. Until now, I’ve never had an issue with GoDaddy certificates where the phone would reject them, but yesterday I renewed the two-year SSL certificate we had (since it expires October 3rd and I don’t want to let it run out–again :-)

So I make it through the renewal process, which required generating a new CSR (Certificate Signing Request) for a brand new certificate from the server since the original one had a bit length of 1024 and GoDaddy only accepts 2048 to 4096 bit lenghts (this is a new requirement). After completing the process and getting the certificate installed, I got a nice helpdesk call from a user this morning who has a Centro: “SSL certificate not accepted due to possible expiration.  Check device date & time and re-sync.”

Joy oh joy, exactly what I’d been looking for, another problem and wasted time!

OK, enough sarcasm (but really, can you ever have enough?). Time for Google and Daryl Hunter from the Church IT Roundtable! Although GoDaddy auto-renewed my SSL certificate, I was actually contemplating buying one of their UCC certificates to be ready for when we went to Exchange 2007. Fortunately I read Daryl Hunter’s post about Exchange 2007 without UCC certs, and stuck with the regular certificate for now, because per Palm KB article 43375, certificates with Subject Alternate Names (SANs), such as UCC certs, are not supported at all on Palm devices (“SSL v3 certificates which rely on the Subject Alternate Name field to do load balancing across virtual site names do not work with Palm OS devices.”). So a UCC cert isn’t even an option for me, but it’s cheaper to do Daryl’s method anyway! For now I don’t have to worry about it, since I just have Exchange 2003 for now, and that’s not the present issue (but we will likely be on Exchange 2007 or Exchange 2010 by the time the certificate expires). Additionally, the same article (which has a tool for installing new trusted root certificates on some Palm OS devices–but I didn’t want to mess with touching every single Palm OS device here! And, the tool works on Windows 2000 or XP only, not Vista (and I’m sure not Windows 7 either)) specifically states that, “GoDaddy Class 2 certificates do not work with Palm OS devices.” Time to drop GoDaddy!

Daryl’s favorite SSL certificate vendor (and now, mine too!) is RapidSSL Online. They sell certificates from RapidSSL.com for $17.95 per year (or cheaper, for multiple years), and they’re single root certificates (which menas you don’t have to install intermediate certificates on your server). While RapidSSL Online is cheap, RapidSSL.com directly has a 30 day trial certificate you can sign up for to test for a month, and this is the way I went. When that certificate expires I’ll be purchasing a multi-year certificate from RapidSSL Online, but I wanted to make sure it would work, and it does! I don’t know for sure, but it appears that RapidSSL.com is the company holding the root certificate, while RapidSSL Online is either a reseller or a sub-company of the parent selling the certificates at a discount (the RapidSSL.com certificates aren’t expenive but still cost a lot more than from RapidSSL Online!). Either way, RapidSSL Online claims that their RapidSSL certificates are issued by RapidSSL.com so they should be the same (I haven’t made a purchase yet), and Daryl Hunter has used RapidSSL Online successfully for years across multiple installations.

I generated a new CSR for a new certificate, again (just like I had to do for GoDaddy). I installed the free certificate on my Exchange server’s IIS (I also then exported it and imported the .pfx file onto my ISA 2004 firewall since it does the authentication up front for external clients, but that’s a pretty unique case and in most cases you want this done on the Exchange server). They were right, it’s just a single root on the certificate, signed by Equifax! I had my Palm Centro users (two had complained by this point) try syncing again. It worked! My iPhone also works fine still, and I haven’t had any negative reports from the four Palm Pre users here either. None of my users have Windows Mobile, and my one Blackberry user connects though Blackberry Professional Server rather than with ActiveSync.

So, adios GoDaddy SSL; fortunately they will refund all but $15 of my certificate (for processing since it was issued), and I’ll still come out ahead with RapidSSL Online (GoDaddy was $60 for two years, while RapidSSL Online is only $70 for five years!).

One thing I’ll have to be careful of when I go to Exchange 2007 is that once I use Windows Server 2008 to generate the CSR, it appears I will need to go to extra pains to make sure the CSR is in Printstring format instead of UTF-8, as Palm OS doesn’t support UTF-8 certificates either (Server 2003 uses Printstring by default). Daryl located this useful post while helping me troubleshoot: Ranting about Palm Centro Versamail ActiveSync and SBS 2008. Useful info, I’m sure I’ll be going back when it’s time to renew next time and Server 2008 is in place. By then, I hope we are Palm OS-free; although I loved my Treo 600 and Treo 650 both, the web is littered with forum and blog posts from people who have SSL issues with Palm OS devices (the Palm Pre and Pixi are much more flexible and up-to-date with the Palm WebOS). I was happy GoDaddy “just worked” in the past, frustrated that they “just didn’t work” this time, and happy to save money and move to a company that’s quicker/faster/easier!