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Other possible measures which might be more or less feasible are:

1. Measure web traffic at sagemath.org, especially around the Downloads and documentation sections. Although sage comes with its own documentation, I suspect that a lot of users gravitate toward the online version because that's what google finds.

2. Measure usage of the public notebook servers

3. Another eventual way to get numbers would be through the notebook -- something like a popup for the first time the notebook is run with a short explanation and buttons like "Yes, send anonymous usage data to sagemath.org", "No, never send data to sagemath.org", and "Not right now, but ask me again later." Although some users might prefer the command line eventually, I think it's a safe bet that the vast majority will open the notebook at least once.

p.s. I think an upgrade reminder is a useful idea anyway -- when I started using sage, I had no idea how quickly new versions are released!

Other possible measures which might be more or less feasible are:

1. Measure web traffic at sagemath.org, especially around the Downloads and documentation sections. Although sage comes with its own documentation, I suspect that a lot of users gravitate toward the online version because that's what google finds.

2. Measure usage of the public notebook servers

3. Put a poll on sagemath.org, with questions which could help determine the mystery ratios of how many sage users subscribe to sage-support, or how frequently people download new binary distributions.

4. Another eventual way to get numbers would be through the notebook -- something like a popup for the first time the notebook is run with a short explanation and buttons like "Yes, send anonymous usage data to sagemath.org", "No, never send data to sagemath.org", and "Not right now, but ask me again later." Although some users might prefer the command line eventually, I think it's a safe bet that the vast majority will open the notebook at least once.

p.s. I think an upgrade reminder is a useful idea anyway -- when I started using sage, I had no idea how quickly new versions are released!