On 29/04/2021 17:41, Jim Garrison via Cygwin wrote:
I got the "newer version" prompt just now when running setup and
downloaded 2.908 (I was on 2.905).

Now I'm seeing really flaky behavior in 2.908

[...]

* "This version of setup is *older* than the one you used last time"


I guess the message here is "setup.ini is older than the one you used last time you installed cygwin."

This indicates that (setup thinks that) the timestamp in the retrieved setup.ini file has gone backwards.

(determined by comparing the value saved in /etc/setup/timestamp with that given by the setup-timestamp: line close to the beginning of setup.ini)

  Does not happen the first time the new setup is launched, but then
  occurs intermittently thereafter.  I saw that message on two
  occasions, and the second time setup-x86_64.exe crashed a few
  seconds later. No message, the window just closed after I dismissed
  the message popup.

  Note: When I downloaded the new setup-x86_64.exe I overwrote the
  old one, so there's no chance (barring an OS caching bug) I was
  running 2.905 at that point.

There haven't really been any setup changes in the relevant area.

The only thing I can think of is that it's possible that your mirror URL might have been upgraded from http to https, which might effect how any proxy you are behind is working.

Some old setup versions are available at [1], if you want to downgrade.

[1] https://cygwin.com/setup/

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