I’ve been thinking about how to do this recently with Bitter. When you have an update for your application that you want your users to have, how should you push it down? I see four distinct levels of updating:

Manual Check and Web Page Download

You can require the user to manually go the web page, check for a new version, download it and copy it over the old application. This is obviously the worse way to go from a usability perspective, but also requires little to no work for the developer (other than packaging up the new version). This is probably ok for applications that are seldom used, not popular, or maybe only for a select group of users, but not ok for anything other than that.

Automatic Check and Web Page Download

In this scenario, the application would automatically check for updates and alert the user of such, but would still require the user to actively download and “reinstall” the application. This only requires the application to download a file stored on the file that contains the currently released version number and compare it against it own. The developer would also need to manage the version number file and update it accordingly. Not difficult to accomplish and it gives you a little more bang for your buck.

Automatic Check and Automatic Download

With this version, the application would both check and compare the versions and then would automatically download the new version of the application with the user’s approval. It may also even copy the application in place over itself and restart the application. This is what I’ve currently done with Bitter as I document in this post. This is still not that hard to accomplish. In .NET, I showed that doing this is only about 10 lines of code of any real meat (not counting exception handling, logging and message boxing).

Automatic Check and Automatic Install

Here the application automatically checks for updates and automatically installs updates. No user intervention required or possible.

So what’s the best way to go? With Automatic Check and Automatic Download, the user still has to tell the application to download and install the updates. It’s up to the user. In Automatic Check and Automatic Install, the user has no choice. He is going to get the update or he ain’t running the application.

One of my new favorite applications Digsby, uses the Automatic Check and Automatic Install approach. When you login, it will check for updates and automatically install them. You don’t have a choice. This is good because the user doesn’t have to do anything special. They will always be up to date. This is good for the developer too, since the developer knows that if you are running the application you will have the latest version (or at least the next time you start). But what if you don’t want the update? It’s not uncommon for developers to introduce new features as well as new bugs into an application in an update. If you know about the new bug introduced in the next version, but need to login, what are you going to do? You don’t have a choice but to accept the update, get the bug, and hope another update with the bug fixed will be coming soon (and hope that no other additional bugs will be introduced as well).

On the other hand, if you don’t force updates, your user base could become this heterogeneous mixture of versions that you have to support and that your website has to support. If version 1.0 is checking for updates in a certain path, but the current version is checking for updates in another path, you either need to support both paths for an indeterminate amount of time or just let v1.0 break. Not only that, but users running older versions might request features that are already fixed and they have no real obligation or motivation to move to the next version. They could stay there using v1.0 until our insect overlords come and take over. Is that ok (the versioning thing not the insect thing)?

One more facet to consider with support is that businesses typically want to test Windows updates before deploying them across their organization. This often means that organizations and the multitudes of computers behind them can be several versions behind the current one in whichever OS they are using. If this describes the situation of your application, then the decision is already made for you. No auto updating otherwise your application will be passed up for another that does allow less-automatic update installation. However, most of us (thankfully?) aren’t in that category.

Arguably one of the best if not the best free Photoshop-like applications out there, Paint.NET, does not force you to update. It shows you that an update is available when you start up the application and you can check for updates through the menu, but you aren’t forced to update. And you know where it’s gotten them? I’m running version 3.10 on both of my home computers even though the current version is 3.31. I’ve seen the update dialog for months now and still haven’t installed the update. I’ve not intentionally not installed the application, it’s just that the version I have seems to work fine and I really don’t know how much trouble it will be or how long it will take to install the new version even though I’ve never tried. I simply don’t want to be bothered with it.

Where does that leave us?

The Automatic Check and Automatic Download method gives the user more control and keeps the user in the loop, but… it keeps the user in the loop. Most users don’t care about versions, they always want the latest. That may mean that we should use the Automatic Check and Automatic Install method, right? But doing that will piss off the 1% of users that actually want to control their versions let alone the business users. And what’s worse is that this method is all or nothing. You can’t let most users automatically update and then let other users choose which version they want. If that’s the case, then you’re automatically back in the Automatic Check and Automatic Download way of things with the support troubles and versioning nightmare.

So what’s it going be? Should you just cater to the common case or do you want to attempt to make all your users happy?