Cask Bookends not upgrading to 15.4.3

[bobtodd]

Output of brew config

HOMEBREW_VERSION: 6.0.20
ORIGIN: https://github.com/Homebrew/brew
HEAD: 3e3da86e4eaccd23f4ce43df9b0a31b16c707347
Last commit: 4 days ago
Branch: stable
Core tap: N/A
Core cask tap: N/A
HOMEBREW_PREFIX: /opt/homebrew
Homebrew Ruby: 4.0.6 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/4.0.6/bin/ruby
CPU: 16-core 64-bit arm_palma
Clang: 21.0.0 build 2100
Git: 2.50.1 => /Library/Developer/CommandLineTools/usr/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 26.6.2-arm64
CLT: 26.6.0.0.1781586589
Xcode: 26.6
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
working fine: please don't worry or file an issue; just ignore this. Thanks!

Warning: Some installed casks are deprecated or disabled.
You should find replacements for the following casks:
djview

Warning: Some installed formulae are deprecated or disabled.
You should find replacements for the following formulae:
    icu4c@76

Description of issue

Howdy y'all,

I've switched in the last month to managing the Bookends app via Homebrew as a Cask. According to the formula for Bookends, 15.4.3 is the current stable release. But when I run brew upgrade --cask bookends, the app that opens has the previous version 15.4.2 (and gives me a prompt asking if I want to upgrade directly from the site). This still happens if I use the --greedy flag, and even if I do brew reinstall instead.

I've mentioned this on the Bookends support forum, but the suggestion was to ask here.

Does anyone else see this behavior? Is there something I'm doing wrong or forgetting to do?

Peace out,
Todd

Relevant casks

bookends

[SMillerDev]

Does the same happen if you install it from the URL in the cask?

If it does, they are somehow serving the wrong version and only the upstream developers can fix it.
If it does not, can you run brew info --cask --verbose bookends and post the output here?

[bobtodd]

Good question! I used the link, and that installed the correct version, 15.4.3.

I ran brew info --cask --verbose bookends, and this was the output:

==> bookends ✔ (Bookends): 15.4.3
Reference management and bibliography software
https://www.sonnysoftware.com/bookends-for-mac
Installed (on request)
/opt/homebrew/Caskroom/bookends/15.4.3 (391.9MB)
  Installed using the internal formulae.brew.sh API on 2026-08-27 at 11:19:13
From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/b/bookends.rb
==> Requirements
Required: macOS >= 11 ✔
==> Artifacts
Bookends.app (App)
==> Analytics
==> install (30 days)
Index | Name (with options)                                                                                               | Count |  Percent
-----:|-------------------------------------------------------------------------------------------------------------------|------:|--------:
1     | bookends                                                                                                          |    22 |  100.00%
==> install (90 days)
Index | Name (with options)                                                                                               | Count |  Percent
-----:|-------------------------------------------------------------------------------------------------------------------|------:|--------:
1     | bookends                                                                                                          |    62 |  100.00%
==> install (365 days)
Index | Name (with options)                                                                                               | Count |  Percent
-----:|-------------------------------------------------------------------------------------------------------------------|------:|--------:
1     | bookends                                                                                                          |   220 |  100.00%

[bobtodd]

I think I get what you're saying. But can I ask, if you use the link https://www.sonnysoftware.com/bookends-for-mac/downloads/Bookends.dmg, what version does it install for you? If I do it straight from the website via that link, it installs the current version, just as the developer set it up to do. I'm not quite sure why, when brew upgrade --cask says it's hitting the same link, I get a different result. Perhaps Homebrew downloads from the site, but installs an earlier cached file for some reason? Or perhaps it says it downloads, but doesn't? If Homebrew saved the downloaded files renamed with version numbers (I don't know if it does that already), would that force it to install the most recent download?

In the end, my comment above shows Homebrew thinking it installed 15.4.3, which it didn't. Then I installed it by hand. And now Homebrew thinks it upgraded Bookends to 15.4.4, but it's back to 15.4.2. So it's effectively downgrading my version...

[cho-m]

You may want to check what is downloaded at $(brew --cache bookends).

Perhaps try removing the file and then provide output of:

HOMEBREW_DOWNLOAD_CONCURRENCY=1 brew reinstall --debug --verbose bookends

which will output curl command used to download.

If:

• it picks older version, then caching is happening outside of Homebrew. You will need to find out where.
• it picks correct version, then caching may be within Homebrew/brew. Could be a regression as I think we did clear the old cache entries prior to downloading new one for unversioned Cask urls but haven't checked code in a while.

EDIT: Also, as mentioned by others, upgrading unversioned url is best effort. Unless upstream provides an actual versioned url that remains stable across versions (not the workaround they listed), Homebrew cannot verify the download is correct. So if a Cask uses a regional rollout, then it is possible that upgrade will not work correctly.

[bobtodd]

Howdy,

Thanks. That was helpful. That procedure worked. It successfully installed the newest version, 15.4.4.

Here's the output it gave:

(base) ~> ls "$(brew --cache bookends)"
~/Library/Caches/Homebrew/downloads/2df4c8a1f45ca91bb4f15d02c9c34488fc1cd18f03ac248188b9edcd270671eb--Bookends.dmg

(base) ~> mv ~/Library/Caches/Homebrew/downloads/2df4c8a1f45ca91bb4f15d02c9c34488fc1cd18f03ac248188b9edcd270671eb--Bookends.dmg Desktop 

(base) ~> ls "$(brew --cache bookends)"
ls: ~/Library/Caches/Homebrew/downloads/2df4c8a1f45ca91bb4f15d02c9c34488fc1cd18f03ac248188b9edcd270671eb--Bookends.dmg: No such file or directory

(base) ~> HOMEBREW_DOWNLOAD_CONCURRENCY=1 brew reinstall --debug --verbose bookends
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading bookends
==> Would reinstall 1 cask:
bookends
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/6.0.22\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 26.6.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 -V
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/6.0.22\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 26.6.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head https://www.sonnysoftware.com/bookends-for-mac/downloads/Bookends.dmg
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/6.0.22\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 26.6.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head --request GET --http1.1 https://www.sonnysoftware.com/bookends-for-mac/downloads/Bookends.dmg
==> Fetching downloads for: bookends
==> Downloading https://www.sonnysoftware.com/bookends-for-mac/downloads/Bookends.dmg
==> Downloading from https://www.sonnysoftware.com/media/pages/bookends-for-mac/downloads/01de72d1f2-1788954420/Bookends.dmg
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/6.0.22\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 26.6.2\)\ curl/8.7.1 --header Accept-Language:\ en --fail --retry 3 --remote-time --output ~/Library/Caches/Homebrew/downloads/2df4c8a1f45ca91bb4f15d02c9c34488fc1cd18f03ac248188b9edcd270671eb--Bookends.dmg.incomplete --location https://www.sonnysoftware.com/media/pages/bookends-for-mac/downloads/01de72d1f2-1788954420/Bookends.dmg

...

==> Verifying Gatekeeper status of ~/Library/Caches/Homebrew/downloads/2df4c8a1f45ca91bb4f15d02c9c34488fc1cd18f03ac248188b9edcd270671eb--Bookends.dmg
/usr/bin/env /usr/bin/xattr -p com.apple.quarantine ~/Library/Caches/Homebrew/downloads/2df4c8a1f45ca91bb4f15d02c9c34488fc1cd18f03ac248188b9edcd270671eb--Bookends.dmg
...

... followed by the rest of the install. This seems to fall within your scenario of caching within Homebrew.

In fact, it seems that it re-uses the exact same hash it had before (2df4c8a1f45ca91bb4f15d02c9c34488fc1cd18f03ac248188b9edcd270671eb) to name the downloaded file.

Please let me know if you'd like me to send along any other logs or environment checks to help trace the source of the behavior.

Peace out.

[cho-m]

@bevanjkay added a fix in Homebrew/brew#23917. It will be part of brew 7.0.0 so you can try again when that is available and new Bookends is released.