How to sync a vintage Windows CE Pocket or Handheld PC to iOS or Android using Nextcloud

Note 0: Windows XP is unsupported and potentially insecure. Running a web server with your personal data without HTTPS is a recipe for disaster. Know what you are doing and make sure only allowed devices, addresses and networks can reach it.
Note 1: I am really sorry for the poor audio quality. It’s very loud in here today. There’s not much I can do about it.
Note 2: Many thanks to Salvo Isaja for putting this together.
Note 3: I haven’t explicitly mentioned Android or Windows in the video but the process is the same. Add the same CalDAV, maybe CardDAV, to your modern device and it will synchronise just fine.

In my opinion, the best personal information manager ever released is the one Microsoft shipped with the earliest versions of Windows CE Handheld. The interface is simple, with a very high information density. The devices are fast and elegant, offering a distraction-free computing experience.

However, Microsoft doesn’t support synchronising these devices with Windows 7 without ActiveSync. Only the newest versions are support, and these don’t come with the PIM apps.

It’s important for me not to risk losing the data I have in these devices. Moreover, not always I have them with me when I need the data. Open source to the rescue!

With a Windows XP SP3 VM, Outlook 2007 SP3, ActiveSync and a local Nextcloud server or any other CalDAV server, you can synchronise your ancient Handheld or Pocket PC, keeping it useful and helping protect the environment.

Instructions:
1. Install Windows XP SP3 and Outlook 2007 SP3.
2. Install the .NET framework 4.0 full profile from microsoft.com/en-us/download/details.aspx?id=17….
3. Install the .NET patch KB2468871 from microsoft.com/download/details.aspx?id=3556
4. Install the Visual Studio Tools for Office VSTO version 10.0.50903 from download.microsoft.com/download/C/0/0/C001737F-… - due the issues described here stackoverflow.com/questions/32806546/vsto-2010-…, you must use the version specified.
5. Install the Primary Interop Assembly (PIA) for Outlook 2007. Microsoft doesn’t offer it anymore. Use Google. If your Windows CE device is supported by Windows 7, use the newer and better maintained sourceforge.net/projects/outlookcaldavsynchroni…
6. Install ActiveSync 3.6.
7. Download and run the installer.

Fixing the problems:
Launch Outlook and remove the add-on. (Tools - Trust Center - Add-ins - click the Go button).
The installer is missing some files. Retrieve from the depository the following files:
1. LICENSE.txt
2. LogoBanner.bmp
3. outlookcaldavsynchronizerlogoarrow.png
sourceforge.net/projects/outlookcaldavsynchroni…

Move the LICENSE.txt to C:\Program Files\caldavsynchronizer.
Move the other two files to C:\Program Files\caldavsynchronizer\Resources.

Now go to C:\Program Files\caldavsynchronizer and run caldavsynchronizer.vsto.

Outlook configuration:
1. Make sure the Add-in is running.
2. Go to Synchronization Profiles.
3. Click Add and choose Nextcloud.
4. Select a Calendar or Tasks folder as Outlook folder.
5. The DAV URL will have the following format: server/remote.php/dav/calendars/user_name/calen… - don't forget the ending slash. The automatic discovery seems to be broken, so you must enter the full calendar path. SSL/TLS seem to be broken. Your server must allow HTTP plain-text only. EXTREMELY INSECURE - you must know what you are doing and do it in your own network and servers only.
6. Be careful choosing the right Synchronization Mode if you are synchronising an existing account.
7. Test the settings, click OK to confirm.
8. Click Synchronize on the main Outlook toolbar and enjoy.

If you have added your Nextcloud account (or any other CalDAV server that you host) to your modern smartphone and computer, you should see all Calendar entries and tasks (including categories and notes) synchronising perfectly. Items created on your Windows CE device will sync to your modern devices and vice-versa. Task completion, calendar entries and alert settings work fine.

Episode index:
00:00 - A horrible introduction
00:28 - Requirements
00:58 - .NET Framework 4
01:20 - .NET Framework 4 KB2468871
01:45 - Visual Studio Tools for Office (VSTO) 10.0.50903
01:59 - Primary Interop Assembly (PIA) for Office 2007
02:16 - Outlook CalDav Synchronizer for Win XP
02:43 - Broken Add-in
03:16 - Adding missing files to the installation folder
04:27 - Configuring your CalDAV / Nextcloud account
05:35 - The result


Hardware:
- Classic Mac Pro.
- Compaq Aero 8000 WinCE 2.11, Pocket Outlook version 3.01, 16MB of RAM from 1999.
- HP Jornada 720 WinCE 3.0 2000, Pocket Outlook version 3.1, 32MB of RAM from 2000.

Software:
- Windows CE
- Microsoft ActiveSync 3.6
- Windows XP SP3
- Outlook 2007 SP3
- Nextcloud CalDAV server
- VirtualBox