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I'm hoping my efforts of the past couple of days, which I am documenting below, will assist others.  This is not a post meant to specify "The Right/Only Way" to do this, merely the way that I've been able to make workable as of this date.

The Problem Solved:

You want to continue using Outlook.  You purchased a new Droid and want to sync email, calendar, contacts, and tasks between outlook and your phone, with a SmarterMail server as the go-between so that you can also access this same information via webmail when necessary.  You don't want to use Google's cloud as the go-between.  You don't want to have to jump through hoops, swing a dead cat and say a chant to make it all work.

The Issues You'll Run Into:

SmarterMail can propose a few different ways of going about this, using a few different apps.  In my case, the funambol 100% SyncML solution did not work -- the plugin for Outlook would not connect to SmarterMail, and the Droid version of the funambol client was very limited in features -- pretty much calendar only from what I could see.  The Exchange client that comes with Droid is limited.  SmarterMail can never look like an exchange server to outlook, so POP3 or IMAP are still required for messaging.  But smartermail can be made to look like an exchange server to mobile devices.

The Investments You'll Have To Make:

Aside from the Droid and the Outlook license, you'll need the following in order to make my solution work for you:

1.  SmarterMail Enterprise 6 (free to unlimited cost based on number of mailboxes, see SmarterMail product pricing on their website)

2.  The ActiveSync license for your SmarterMail installation ($199 and up, see SmarterMail product pricing on their website; free trial available via your SmarterMail server admin interface in webmail)

3.  The SmarterMail Sync plugin for Outlook (free)

4.  An application called "Touchdown" by a company called NitroDesk Inc., which is available from the Droid Market.  Search for "Exchange for Android" and install the app for Android 2.0/2.1.  The app has a 5 day trial and is $20 to purchase.

The way this works from here is actually pretty simple:

You set up Outlook to connect to your SmarterMail mailbox using either IMAP (if you want to keep all messages and message folders on the server) or POP3 with the setting to leave messages on the server X number of days turned on.

You install smartermail sync and configure it in outlook.

You verify that your calendar, contacts, tasks and notes can be sync'd between Outlook and webmail, bi-directionally (changes in one are reflected in the other).  You also verify that IMAP or POP3-with-messages-left-on-server is working.

You then install the activesync license to your SmarterMail server and configure your mailbox as an activesync-capable mailbox.

You install Touchdown on your droid, and point it at your SmarterMail server.  It will pull in all calendar, contacts, and tasks (hereafter referred to as "CCT"; notes are not supported at this time).

You set Touchdown for "push" retrieval or you can set it to simply hit the server x number of minutes for updates to CCT.

Touchdown is your primary client on the phone for email, calendar, contacts and tasks

You can run a manual sync in Outlook when you want something pushed to the server (and hence to your phone) immediately, or you can set SmarterMail Sync to do a sync when starting and/or closing Outlook.

This really is the only way I've found to get near-instant reliable sync between Outlook, webmail, and a Droid, bi-directionally, without complications.  The exchange client built into Droid is limited at best, and it looks as if NitroDesk is actively working on upgrades to Touchdown so it's continually improving.

This configuration has made my Droid useful for business, whereas before I was completely disconnected from business because everything was in Outlook only.  It's reassuring too, to know that my critical email/calendar/contact/task data is actually available in three places now, in case Something Bad should happen in any one place...

I'm sure I haven't discovered all the limitations, and I certainly haven't researched all other possibilities (but darn close!).  This config works for me, as the owner of a Droid -- cutting edge technology as of this writing.  It may or may not suit your needs, but this should save you some time finding out.  The Droid does rock...

Post here if you would like to ask some specific configuration questions; I'll help where I can.

This is a great solution that makes the Droid a true business tool.  Touchdown is what Google should have included with the Droid!

I have this same configuration, but I took the Outlook integration one step further and used SyncML from Outlook <-> SM6.  This gives me near real time updates from Outlook <> SM6 <> Droid (3-5 seconds for contact/calendar/note updates).  Just go to your SM6 webmail calendar and click "Add to Outlook" on the toolbar.  This creates a Sharepoint List in Outlook and enables bi-directional push updates.  Touchdown and EAS already have bi-directional push updates.  Very cool solution.

I have come across some limitations or bugs (not sure which yet):

1. Calendar reminders are not updated when calendar events are synced. Neither Outlook <> SM6 nor SM6 <> Touchdown support this.

2. Touchdown does not support creating contacts from the Droid call list.

3. When Outlook POPs an email from SM6, then message is removed from SM, but the delete does not push to the Droid.  When I'm looking at Outlook and a message comes in, I don't want to goto the Droid and "Refresh" to get the delete.  If I wanted that functionality I would have Outlook leave the messages on SM after POP.

I think these are solvable and will only improve a great solution.

Droid Does...

Both 1 and 3 will be fixed in the next release of SmarterMail. For #2 could you use the built in ActiveSync support to only sync your contacts? That's probably what I would do.

I upgraded to Outlook 2007 specifically to try this.  Unfortunately when I clicked on "add to Outlook" in the webmail calendar, it created a SEPARATE calendar in outlook instead of just integrating with Outlook's main calendar.  This makes it impossible for me to create an appointment and "invite" someone to it, or receive invites, because they'd always end up in my main outlook calendar instead of the "SmarterMail" calendar.  Isn't there a way to make this work directly with Outlook's main calendar instead?

Unfortunately, no. SmarterMail uses the same sync technology that SharePoint does and therefore shares the same shortcomings.

Is there an ETA for the next release of SM that will solve these two issues?

I use the calendar functions a lot and this is really crimping my style as I forget things when I'm not reminded!

I have confirmed with Nitrodesk that Touchdown cannot create contacts from the call list at this time.  Perhaps on the road map, but not sure.

Thanks Matt.  I think what will probably be confusing to some newcomers -- maybe -- is that ActiveSync gives SmarterMail "Exchange-like" access, but only for Mobile Devices, and otherwise, the integration with Outlook can't really rival that of an Exchange server.  HOWEVER... if SmarterMail Sync for Outlook could simply monitor for changes in the background and push Calendar/Contact/Task/Note data out to the server on demand, rather than just At-Startup / Manual / At-Shutdown, it would be so close that no reasonable user would care. :)  The original configuration I outlined in my first post is holding up very well for our two-person little company, on both the Motorola Droid and the HTC Droid too.

I was asked by a ST tech person to help with some debugging, and will try to get that information out to them today.

I also found that in the Touchdown calendar app, I could see appointments, but not edit them... maybe it was just the recurring one, I don't know, more testing is needed...

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