After reviewing some code, I think it may just be better to not display any tty message after running the command with --dry-run.

@ngoue Thanks for writing in. I was able to reproduce this bug, definitely a confusing message. Rather than change the output completely, I think we can just fix this message to instead state that there were no extensions that needed to be upgraded.

Can I work on this one?

This has been bugging me since ever and I needed to add this workaround to my crontab entry that monitors updates: gh extension upgrade --dry-run --all | egrep -v ": already up to date$"
Given this help message --dry-run Only display upgrades it would be really beneficial if --dry-run indeed showed only whether an extension needs upgrading. Or maybe adding --quiet to suppress already up to date messages would be enough.

Also trailing message in interactive mode (when the output is not piped) is confusing:

> gh extension upgrade --dry-run --all
[…]
[userfetch]: already up to date
[users]: already up to date
[webhook]: already up to date
✓ Would have upgraded extensions

> gh extension upgrade --dry-run --all | egrep -v ": already up to date$" -c
0

The ✓ Would have upgraded extensions line, that indicates there are some upgrades pending, is erroneous.

Given this help message --dry-run Only display upgrades it would be really beneficial if --dry-run indeed showed only whether an extension needs upgrading

This is a very confusing help message. What it means is "Only display upgrades (rather than actually applying the upgrade)".

The other part is the bug that this issue is capturing.

Just to double check, is the purpose of your cron job simply to determine whether and extensions could be upgraded?

Just to double check, is the purpose of your cron job simply to determine whether and extensions could be upgraded?

Yep, exactly (assuming you mean any rather than and). It simply reports whether any of extensions need upgrading (by listing those that need upgrading) so that an operator can decide what to do with this information.