I noticed a problem with Epocrates synchronization that occurred repeatedly and I figured out the solution and so I share with you the steps needed to get around it.
First of all, this problem happens on Windows Xp machine using Activesync and am not sure if the same applies to Windows Vista – Windows Mobile Device Center combination.
Second, it usually occurs when you reinstall Epocrates Essentials after previous installation (like for example when you get a new device and you want to sync it with the same desktop).
The problem is that after complete installation the synchronization does not start at all and when you check in Activesync Tools>Options you find that Epocrates Autoupdate can not be checked and is not highlighted and unclickable.
To solve the issue
1) On your desktop go to ActiveSync>Tools>Options and un-check all the options that you have it already syncing like notes, favorites, email, other added software, …etc. [ leave only contacts and calendar].
2) Resync the device [ remove it from the cable and reattach and not only resyncing].
3) Now reinstall Epocrates once again by double clicking the installation file you already downloaded from Epocrates.
4) Now go to ActiveSync Tools>Options and you will find that Autoupdate is clickable and so check it with a smile on your face!
5) Resync again and you will be asked for your Epocrates username and password enter it
You will then have your Epocrates running and synced on your device.
Now in order to get back your other options that you have unchecked before in step 1 above, you need to uncheck Epocrates Autoupdate and thereafter continue sycning without Epocrates Autoupdate. There seems to be a problem autoupdating Epocrates with the other options. So just go without Epocrates update.
In the future if you want to update Epocrates you need to again unsync all your options leaving only contacts and calendar [steps 1 to 4 skipping step 3].
Or even better just sync wirelessly and don’t ever sync again via ActiveSync. Of course you need WiFi or GPRS access to do that. The steps shown here:
Tags: Epocrates
Strc21 
AESCA 
Thank you this is exactly what I’ve been looking for!
Thanks for taking the time to describe your solution and with screenshots too! However, my problem with epocrates does not seem to be fixed by your recommendation.
I have always been able to check the AuotUpdate box in the Tools> Options. All my firewalls are down as is anti-virus programs. I keep getting the message that a connection cannot be established with their server. The server address is correct as is also my username and password. I have done this several times.
Luckily I found the solution on Mobilitysite and here’s how;
Uncheck the AutoUpdate option from ActiveSync>Tools>Options then update manually from Epocrates itself while the device is still connected to the desktop.
This you’ll have AutoUpdate guaranteed