Restful design, Open formats and an Outlook Add-In

We mostly work with startups, and most prefer using dynamic languages like Ruby and Python. Occasionally though, we have worked on .NET/Java projects because they were really interesting. One such project was to build an Outlook add-in to synchronize mails, contacts and calendar to a CRM system. There was already an existing add-in we were replacing, because it had lots of bugs, and its performance was bad. We analyzed the problems with the existing design and moved towards a more RESTful design. Using a RESTful design helped us in several ways:

1. Crisp protocol between server and client.

The existing plugin and the server communicated over a SOAP based protocol. The protocol was RPCish, and this resulted in the protocol being very chatty. We were pretty sure that this would have caused performance issues for even moderate data. This also meant that there was a tight coupling between the server and the client - more service methods under contract makes it difficult to change either of the service or the client code independently.

To avoid these problems, we exposed the server code as a RESTful web service. We identified resources (Appointments, Contacts and Emails) and standard operations available on these - using HTTP verbs (GET/POST/DELETE/PUT). The behaviour of these methods are well-understood. The fact that the service was over HTTP, makes it easy to implement the client - most libraries come with a standard HTTP client class. .NET exposes a very good HTTP Client as well.

We did break the REST in a couple of ways - we used POST as a “patch” method equivalent and had to introduce a “keep” method to explicitly synchronize the appointments due to 2 reaons: a) Outlook add-in APIs don’t provide hooks to deletions on the client in a clean way and b) avoid client-side performance issues.

2. Server client responsibilities

One of the nice side-effects of REST is that, when you identify the resources correctly, the responsibility of the server and client falls in place - server lists the contacts/appointments when requested for the list of these and updates the resources when it receives a POST. The server is not responsible for making sure that the sync happens correctly, it is the responsibility of the client. Keeping track of the synchronization - last synchronization time, time differences between the server and client etc, are again the responsibilities of the client.

The older add-in code stored the IDs of the outlook appointments/contacts/emails on the server. First of all, this information does not belong to the server, and then this also ties the server to a particular client. We avoided this to allow for synchronizations across multiple clients at the same time. This enables the users to install the same client on more than one machine, and still keeping all different systems in sync.

3. Open formats and standards

This was one of the first decisions we made, as this would help in better interoperability. Individual contacts were represented using vCard, appointments using iCalendar formats. This made it possible to subscribe to the appointments from any device that supports the iCalendar over HTTP - iPhone, Android and other smart phones, Mac OS X and Linux. We looked at using SyncML and ActiveSync protocols for the synchronizations. ActiveSync was out of question, as it was a proprietory. We finally ended up using a custom XML based protocol for emails and contacts, as there was no easily implementable standards for them.


Testing in general was a challenge on this project. Outlook add-in APIs are basically wrappers over COM based APIs. These COM objects are inherently untestable. Mocking wasn’t of much help, as we were starting to see unmaintainable tests with very little value. We tried to get some automated functional tests using a library called White. But Outlook UI turned out to be very difficult to automate, and the effort in writing these tests was too much to be beneficial.

Another challenge was the limitations of the Outlook APIs (there is no easy way to get notified of deletions), the fact that we had different synchronization strategies for Contacts, Appointments and Emails didn’t help the cause either.

Sometimes, hard problems need a small experienced team, and a new perspective.

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