Download fails, but upgrade tries to continue, hanging

[johnwhitington]

Output of brew config

HOMEBREW_VERSION: 5.0.13-67-gcf63ae0
ORIGIN: https://github.com/Homebrew/brew
HEAD: cf63ae09fd3aa6deab9b8c6137835a288b101d64
Last commit: 2 hours ago
Branch: main
Core tap HEAD: d952e3142efb98ef662bc1c044d644f6716bf084
Core tap last commit: 9 months ago
Core tap branch: cpdf
Core tap JSON: 06 Feb 12:06 UTC
Core cask tap HEAD: a86de7529d73b6be87ac60a03edebde6beabcbfb
Core cask tap last commit: 9 months ago
Core cask tap JSON: 06 Feb 12:06 UTC
HOMEBREW_PREFIX: /opt/homebrew
HOMEBREW_CASK_OPTS: []
HOMEBREW_DISPLAY: /private/tmp/com.apple.launchd.oj6ZQr9W0g/org.xquartz:0
HOMEBREW_DOWNLOAD_CONCURRENCY: 16
HOMEBREW_FORBID_PACKAGES_FROM_PATHS: set
HOMEBREW_MAKE_JOBS: 8
HOMEBREW_SORBET_RUNTIME: set
Homebrew Ruby: 3.4.8 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.8/bin/ruby
CPU: octa-core 64-bit arm_firestorm_icestorm
Clang: 17.0.0 build 1700
Git: 2.50.1 => /Applications/Xcode.app/Contents/Developer/usr/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 26.2-arm64
CLT: 26.2.0.0.1.1764812424
Xcode: 26.2
Metal Toolchain: N/A
Rosetta 2: false

Output of brew doctor

Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
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Warning: Some installed formulae are deprecated or disabled.
You should find replacements for the following formulae:
  icu4c@77
  python@3.9

Warning: Unbrewed dylibs were found in /usr/local/lib.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae and may need to be deleted.

Unexpected dylibs:
  /usr/local/lib/libqpdf.28.dylib

Warning: Unbrewed header files were found in /usr/local/include.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae and may need to be deleted.

Unexpected header files:
  /usr/local/include/mupdf/*

Warning: Unbrewed static libraries were found in /usr/local/lib.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae and may need to be deleted.

Unexpected static libraries:
  /usr/local/lib/libmupdf-third.a
  /usr/local/lib/libmupdf.a

Warning: You have unlinked kegs in your Cellar.
Leaving kegs unlinked can lead to build-trouble and cause formulae that depend on
those kegs to fail to run properly once built. Run `brew link` on these:
  opam
  pybind11
  xpdf

Warning: You have uncommitted modifications to Homebrew/homebrew-core.
If this is a surprise to you, then you should stash these modifications.
Stashing returns Homebrew to a pristine state but can be undone
should you later need to do so for some reason.
  git -C "/opt/homebrew/Library/Taps/homebrew/homebrew-core" stash -u && git -C "/opt/homebrew/Library/Taps/homebrew/homebrew-core" clean -d -f

Uncommitted files:
   M Formula/c/cpdf.rb

Warning: Some taps are not on the default git origin branch and may not receive
updates. If this is a surprise to you, check out the default branch with:
  git -C $(brew --repo homebrew/core) checkout main
  git -C $(brew --repo homebrew/cask) checkout main

Warning: Homebrew's "sbin" was not found in your PATH but you have installed
formulae that put executables in /opt/homebrew/sbin.
Consider setting your PATH for example like so:
  echo 'export PATH="/opt/homebrew/sbin:$PATH"' >> /Users/john/.bash_profile

Description of issue

Brew seems to try to upgrade a package even when the download fails. It then fails to make progress...

$ brew upgrade

(snipped)

==> Fetching downloads for: calibre
✘ Cask calibre (9.2.0) #############################                   Downloading 209.5MB/338.4MB
Error: Download failed on Cask 'calibre' with message: Download failed: https://download.calibre-ebook.com/9.2.0/calibre-9.2.0.dmg
==> Upgrading 1 outdated package:
calibre 9.1.0 -> 9.2.0
==> Upgrading calibre
^C

$ brew upgrade
✔︎ JSON API cask.jws.json                                                                              Downloaded   15.3MB/ 15.3MB
✔︎ JSON API formula.jws.json                                                                           Downloaded   32.0MB/ 32.0MB
==> Casks with 'auto_updates true' or 'version :latest' will not be upgraded; pass `--greedy` to upgrade them.
==> Fetching downloads for: calibre
✔︎ Cask calibre (9.2.0)                                                                                Verified    338.4MB/338.4MB
==> Upgrading 1 outdated package:
calibre 9.1.0 -> 9.2.0
==> Upgrading calibre
==> Backing App 'calibre.app' up to '/opt/homebrew/Caskroom/calibre/9.1.0/calibre.app'

(upgrade completes correctly second time)

Correct behaviour, presumably, is that it should bail out when the download fails, and continue with any other upgrade tasks which could succeed.