#Communication When do your users usually work on the site? If the site's users and authors are typically 9-5 corporate in nature, update the site off-hours when less people are going to be working or visiting on the site. And if you think downtime is going to more than a few minutes, inform them of the maintenance window.

#Engineering

Communication

When do your users usually work on the site? If the site's users and authors are typically 9-5 corporate in nature, update the site off-hours when less people are going to be working or visiting on the site. And if you think downtime is going to more than a few minutes, inform them of the maintenance window.

Engineering

As you alluded to, how you answer question 1) is going to inform 2).

You can minimize that chance of messing up a user's work by doing a few things to proactively protect against downtime and frame user's expectations:

#Communication When do your users usually work on the site? If you users are typically corporate, update the site off-hours when less people are going to be working on the site. And if you think downtime is going to more than a few minutes, inform them of the maintenance window.

As you alluded to, how you answer question 1) is going to inform 2). Properly answering question 2) is probably beyond the scope of this Q&A format, but since we're going the down the rabbit hole...

You can minimize that chance of messing up a user's work by doing a few things to proactively protect against downtime and just as importantly, frame the user's expectations:

#Communication When do your users usually work on the site? If the site's users and authors are typically 9-5 corporate in nature, update the site off-hours when less people are going to be working or visiting on the site. And if you think downtime is going to more than a few minutes, inform them of the maintenance window.

I'm probably missing a few things but those are just off the top of my head.

Lindsey D points out that how you deploy can make a difference as well. Deployment services (eg: DeployBot) in coordination with some VPS providers offer atomic deployment. This guarantees that your site remains "untouched" until the new files are 100% uploaded. Using something like Capistrano can do this as well. AWS offers their own set of deploy and server management tools to help manage your uptime too. (Again, you pay the piper for all of this, which is why AWS gives you a year for free in their free tier.)

There's probably a few things you can do but those are just off the top of my head.