From 13df62bbb3a00addf1b9b819fd9d55f7ba05c31c Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 15:36:31 +0900
Subject: [PATCH 01/12] Clean up orphaned release-tag link refs in NEWS.md
 updater

When update-NEWS-gemlist.rb drops a bundled/default gem entry from NEWS.md
(because it no longer differs from the previous-release snapshot), the
matching `[gem-vX.Y.Z]: ...` link definitions were left behind by
update-NEWS-github-release.rb. Detect refs that are no longer cited from
the body and drop them alongside the ones we re-emit, while preserving
defs still referenced by gems whose release range could not be refreshed.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 tool/update-NEWS-github-release.rb | 44 ++++++++++++++++++------------
 1 file changed, 26 insertions(+), 18 deletions(-)

diff --git a/tool/update-NEWS-github-release.rb b/tool/update-NEWS-github-release.rb
index 679e7101a76be8..e10a4d7e7674d4 100755
--- a/tool/update-NEWS-github-release.rb
+++ b/tool/update-NEWS-github-release.rb
@@ -275,36 +275,44 @@ def update_news_md(results)
     i += 1
   end
 
-  # Collect all new footnote links
-  all_footnotes = []
+  # All footnote definitions we can emit from this run, indexed by ref name
+  available_footnotes = {}
   results.each do |r|
     r[:footnote_links].each do |fl|
-      all_footnotes << "[#{fl[:ref]}]: #{fl[:url]}"
+      available_footnotes[fl[:ref]] = "[#{fl[:ref]}]: #{fl[:url]}"
     end
   end
 
-  # Remove any existing footnote links that we are about to add (avoid duplicates)
-  existing_refs = Set.new(all_footnotes.map { |f| f[/^\[([^\]]+)\]:/, 1] })
-  new_lines = new_lines.reject do |line|
-    if line =~ /^\[([^\]]+)\]:\s+https:\/\/github\.com\//
-      existing_refs.include?($1)
-    else
-      false
+  # Refs the regenerated body actually uses (e.g. `][gem-vX.Y.Z]`)
+  used_refs = new_lines.join.scan(/\]\[([^\]]+)\]/).flatten.uniq
+  used_set = used_refs.to_set
+
+  # Drop existing GitHub release-tag link defs that are either orphaned (no
+  # body reference) or about to be re-emitted from this run's results. Defs
+  # still referenced by gems we couldn't refresh are preserved in place.
+  release_ref_pattern = %r{^\[([^\]]+)\]:\s+https://github\.com/[^/]+/[^/]+/releases/tag/}
+  new_lines.reject! do |line|
+    if (m = line.match(release_ref_pattern))
+      ref = m[1]
+      !used_set.include?(ref) || available_footnotes.key?(ref)
     end
   end
 
-  # Ensure the file ends with a newline before adding footnotes
-  unless new_lines.last&.end_with?("\n")
-    new_lines << "\n"
-  end
+  # Trim trailing blank lines so the appended footer block is clean
+  new_lines.pop while new_lines.last == "\n"
+  new_lines << "\n" unless new_lines.last&.end_with?("\n")
 
-  # Append footnote links at the end of the file
-  all_footnotes.each do |footnote|
-    new_lines << "#{footnote}\n"
+  # Append footnote defs only for refs the body still references
+  emitted = 0
+  used_refs.each do |ref|
+    if (footnote = available_footnotes[ref])
+      new_lines << "#{footnote}\n"
+      emitted += 1
+    end
   end
 
   File.write(news_path, new_lines.join)
-  puts "Updated #{news_path} with #{results.length} gem update entries and #{all_footnotes.length} footnote links."
+  puts "Updated #{news_path} with #{results.length} gem update entries and #{emitted} footnote links."
 end
 
 # --- Main ---

From 466f6755935e8446bf67c88ab5cb7e934cf002ff Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 15:41:42 +0900
Subject: [PATCH 02/12] Handle network failures in NEWS.md updater

GitHub API failures (rate limit, transient 5xx, repo missing) used to abort
the whole script mid-run, leaving NEWS.md in a partially regenerated state.
Wrap the per-gem Octokit call so a single failure only skips that gem with
a stderr warning. Centralise stdgems.json and remote NEWS.md fetches behind
http_get so the script aborts with a readable error when the upstream data
source is unreachable, instead of dumping a Net::HTTP backtrace.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 tool/update-NEWS-github-release.rb | 27 ++++++++++++++++++++++-----
 1 file changed, 22 insertions(+), 5 deletions(-)

diff --git a/tool/update-NEWS-github-release.rb b/tool/update-NEWS-github-release.rb
index e10a4d7e7674d4..622c4a495993ef 100755
--- a/tool/update-NEWS-github-release.rb
+++ b/tool/update-NEWS-github-release.rb
@@ -21,7 +21,8 @@
 # Build a gem=>version map from stdgems.org stdgems.json for a given Ruby version (e.g., "3.4")
 def fetch_default_gems_versions(ruby_version)
   uri = URI.parse("https://stdgems.org/stdgems.json")
-  json = JSON.parse(Net::HTTP.get(uri))
+  body = http_get(uri)
+  json = JSON.parse(body)
   gems = json["gems"] || []
 
   map = {}
@@ -92,13 +93,24 @@ def fetch_versions_to_from_news(arg)
   if arg.downcase == "news"
     body = read_local_news_md
   else
-    uri = URI.parse(arg)
-    body = Net::HTTP.get(uri)
+    body = http_get(URI.parse(arg))
   end
 
   parse_stdlib_versions_from_news(body)
 end
 
+# Fetch a URL with a clear abort message on network or HTTP failures.
+# Used for sources whose absence makes the rest of the script meaningless.
+def http_get(uri)
+  res = Net::HTTP.get_response(uri)
+  unless res.is_a?(Net::HTTPSuccess)
+    abort "error: #{uri} returned HTTP #{res.code} #{res.message}"
+  end
+  res.body
+rescue SystemCallError, SocketError, IOError, Net::HTTPError => e
+  abort "error: failed to fetch #{uri}: #{e.class}: #{e.message}"
+end
+
 def read_local_news_md
   news_path = File.join(__dir__, "..", "NEWS.md")
   unless File.exist?(news_path)
@@ -159,8 +171,13 @@ def resolve_repo(name)
 
 def fetch_release_range(name, from_version, to_version, org, repo)
   releases = []
-  Octokit.releases("#{org}/#{repo}").each do |release|
-    releases << release.tag_name
+  begin
+    Octokit.releases("#{org}/#{repo}").each do |release|
+      releases << release.tag_name
+    end
+  rescue Octokit::Error, Faraday::Error => e
+    warn "warning: skipping #{name} (#{org}/#{repo}): #{e.class}: #{e.message}"
+    return nil
   end
 
   # Keep only version-like tags and sort ascending by semantic version

From fbe968e6bf7142586a99de3473807470086df1b8 Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 15:43:13 +0900
Subject: [PATCH 03/12] Drop dead code from NEWS.md updater

* Remove the bundler branch in resolve_repo: collect_gem_updates skips
  bundler before resolve_repo is ever consulted, so the mapping was
  unreachable.
* Inline the gem_name_normalized ternary, which had the same value in both
  arms.
* Remove the unused tag field from footnote_links and switch to map.
* Drop require "set" since Set is autoloaded on supported Ruby versions.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 tool/update-NEWS-github-release.rb | 14 ++++----------
 1 file changed, 4 insertions(+), 10 deletions(-)

diff --git a/tool/update-NEWS-github-release.rb b/tool/update-NEWS-github-release.rb
index 622c4a495993ef..f442fcadfa5f20 100755
--- a/tool/update-NEWS-github-release.rb
+++ b/tool/update-NEWS-github-release.rb
@@ -3,7 +3,6 @@
 require "bundler/inline"
 require "json"
 require "net/http"
-require "set"
 require "uri"
 
 gemfile do
@@ -162,8 +161,6 @@ def resolve_repo(name)
     { repo: name, org: "minitest" }
   when "test-unit"
     { repo: name, org: "test-unit" }
-  when "bundler"
-    { repo: "rubygems", org: "ruby" }
   else
     { repo: name, org: "ruby" }
   end
@@ -209,12 +206,10 @@ def collect_gem_updates(versions_from, versions_to)
     release_range = fetch_release_range(name, versions_from[name], version, org, repo)
     next unless release_range
 
-    footnote_links = []
-    release_range.each do |rel|
-      footnote_links << {
+    footnote_links = release_range.map do |rel|
+      {
         ref: "#{name}-#{rel.sub(/^bundler-/, '')}",
         url: "https://github.com/#{org}/#{repo}/releases/tag/#{rel}",
-        tag: rel.sub(/^bundler-/, ''),
       }
     end
 
@@ -267,12 +262,11 @@ def update_news_md(results)
     # Check if this line is a gem bullet like "* gemname x.y.z"
     if line =~ /^\* ([A-Za-z0-9_\-]+)\s+(\d+(?:\.\d+){0,3})\b/
       gem_name = $1
-      gem_name_normalized = gem_name == "RubyGems" ? "RubyGems" : gem_name
 
       new_lines << line
 
-      if result_by_name.key?(gem_name_normalized)
-        r = result_by_name[gem_name_normalized]
+      if result_by_name.key?(gem_name)
+        r = result_by_name[gem_name]
 
         # Skip any existing sub-bullet lines that follow (lines starting with spaces + *)
         while i + 1 < lines.length && lines[i + 1] =~ /^\s+\*/

From 2885214501e807ca94e2beb8bf4376b21e2d76d9 Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 15:51:43 +0900
Subject: [PATCH 04/12] Read current gem versions from repo state instead of
 NEWS.md

The "to" side of the diff used to come from parsing NEWS.md, which made
this script depend on update-NEWS-gemlist.rb having already written the
right versions there. Read the authoritative sources directly: scan
{ext,lib}/**/*.gemspec for default gems (mirroring the logic in
default_gems_list.yml), pick up the RubyGems version from
lib/rubygems.rb, and load gems/bundled_gems for the bundled set.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 tool/update-NEWS-github-release.rb | 40 +++++++++++++++++++++++++++++-
 1 file changed, 39 insertions(+), 1 deletion(-)

diff --git a/tool/update-NEWS-github-release.rb b/tool/update-NEWS-github-release.rb
index f442fcadfa5f20..7f88f2312383db 100755
--- a/tool/update-NEWS-github-release.rb
+++ b/tool/update-NEWS-github-release.rb
@@ -118,6 +118,44 @@ def read_local_news_md
   File.read(news_path)
 end
 
+# Build a gem=>version map from the current repository state. Default gems
+# come from {ext,lib}/**/*.gemspec (mirroring default_gems_list.yml) and
+# bundled gems come from gems/bundled_gems. This avoids reading NEWS.md as
+# the source of "current versions", which would create a circular dependency
+# with update-NEWS-gemlist.rb.
+def load_current_versions
+  require "rubygems"
+  root = File.expand_path("..", __dir__)
+  map = {}
+
+  rg_path = File.join(root, "lib", "rubygems.rb")
+  if File.exist?(rg_path)
+    File.foreach(rg_path) do |line|
+      if /^\s*VERSION\s*=\s*"([^"]+)"/ =~ line
+        map["RubyGems"] = $1
+        break
+      end
+    end
+  end
+
+  Dir.glob(File.join(root, "{ext,lib}/**/*.gemspec")).each do |path|
+    spec = Gem::Specification.load(path)
+    next unless spec
+    map[spec.name] = spec.version.to_s
+  end
+
+  bundled_path = File.join(root, "gems", "bundled_gems")
+  if File.exist?(bundled_path)
+    File.foreach(bundled_path) do |line|
+      next if line.start_with?("#")
+      name, version = line.split(" ", 3)
+      map[name] = version if name && version
+    end
+  end
+
+  map
+end
+
 def parse_stdlib_versions_from_news(body)
   # Extract the Stdlib updates section
   start_idx = body.index(/^## Stdlib updates$/)
@@ -331,7 +369,7 @@ def update_news_md(results)
 update_mode = ARGV.delete("--update")
 
 versions_from = load_versions(ARGV[0])
-versions_to = load_versions("news")
+versions_to = load_current_versions
 
 results = collect_gem_updates(versions_from, versions_to)
 

From 175062690c5232bd2fcfd273bd1c3c8e58335dcf Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 15:54:12 +0900
Subject: [PATCH 05/12] Extract sub-bullet formatting into format_release_diff

The "  * 1.2.3 to [v1.2.4][gem-v1.2.4], ..." sub-bullet was assembled in
two places with the same expression. Pull it into a single helper so the
formatting and the bundler-prefix stripping live in one spot.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 tool/update-NEWS-github-release.rb | 20 ++++++++++----------
 1 file changed, 10 insertions(+), 10 deletions(-)

diff --git a/tool/update-NEWS-github-release.rb b/tool/update-NEWS-github-release.rb
index 7f88f2312383db..33bb2cccccb1f0 100755
--- a/tool/update-NEWS-github-release.rb
+++ b/tool/update-NEWS-github-release.rb
@@ -263,15 +263,20 @@ def collect_gem_updates(versions_from, versions_to)
   results
 end
 
+def format_release_diff(result)
+  links = result[:release_range].map do |rel|
+    tag = rel.sub(/^bundler-/, "")
+    "[#{tag}][#{result[:name]}-#{tag}]"
+  end
+  "  * #{result[:from_version]} to #{links.join(', ')}"
+end
+
 def print_results(results)
   footnote_lines = []
 
   results.each do |r|
     puts "* #{r[:name]} #{r[:version]}"
-    links = r[:release_range].map { |rel|
-      "[#{rel.sub(/^bundler-/, '')}][#{r[:name]}-#{rel.sub(/^bundler-/, '')}]"
-    }
-    puts "  * #{r[:from_version]} to #{links.join(', ')}"
+    puts format_release_diff(r)
     r[:footnote_links].each do |fl|
       footnote_lines << "[#{fl[:ref]}]: #{fl[:url]}"
     end
@@ -311,12 +316,7 @@ def update_news_md(results)
           i += 1
         end
 
-        # Insert the version diff sub-bullet
-        links = r[:release_range].map { |rel|
-          "[#{rel.sub(/^bundler-/, '')}][#{r[:name]}-#{rel.sub(/^bundler-/, '')}]"
-        }
-        sub_bullet = "  * #{r[:from_version]} to #{links.join(', ')}\n"
-        new_lines << sub_bullet
+        new_lines << "#{format_release_diff(r)}\n"
       end
     else
       new_lines << line

From c45dddeb7197af8037db43c65027300685ae7ba9 Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 16:00:43 +0900
Subject: [PATCH 06/12] Tidy up NEWS.md updater leftovers

* Drop the bundler- tag-prefix handling from fetch_release_range,
  collect_gem_updates, and format_release_diff. collect_gem_updates skips
  the bundler gem before any of these run, so the special-case prefix
  stripping never had a chance to fire.
* Rename fetch_versions_to_from_news to fetch_versions_from_news now that
  the "to" side comes from load_current_versions; the function only
  feeds the "from" baseline.
* Use Enumerable#to_h to build result_by_name, and remove a couple of
  comments that just restate the immediately following code.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 tool/update-NEWS-github-release.rb | 28 +++++++++++-----------------
 1 file changed, 11 insertions(+), 17 deletions(-)

diff --git a/tool/update-NEWS-github-release.rb b/tool/update-NEWS-github-release.rb
index 33bb2cccccb1f0..69e58db5f3be05 100755
--- a/tool/update-NEWS-github-release.rb
+++ b/tool/update-NEWS-github-release.rb
@@ -81,14 +81,14 @@ def load_versions(arg)
   elsif arg.match?(/^\d+\.\d+(?:\.\d+)?$/)
     fetch_default_gems_versions(arg)
   elsif arg.downcase == "news" || arg =~ %r{https?://.*/NEWS\.md}
-    fetch_versions_to_from_news(arg)
+    fetch_versions_from_news(arg)
   else
     abort "Invalid argument: #{arg}. Provide a file path or a Ruby version (e.g., 3.4)."
   end
 end
 
 # Build a gem=>version map by parsing the "## Stdlib updates" section from Ruby's NEWS.md
-def fetch_versions_to_from_news(arg)
+def fetch_versions_from_news(arg)
   if arg.downcase == "news"
     body = read_local_news_md
   else
@@ -216,11 +216,11 @@ def fetch_release_range(name, from_version, to_version, org, repo)
   end
 
   # Keep only version-like tags and sort ascending by semantic version
-  releases = releases.select { |t| t =~ /^v\d/ || t =~ /^\d/ || t =~ /^bundler-\d/ }
-  releases = releases.sort_by { |t| Gem::Version.new(t.sub(/^bundler-/, "").sub(/^v/, "").tr("_", ".")) }
+  releases = releases.select { |t| t =~ /^v\d/ || t =~ /^\d/ }
+  releases = releases.sort_by { |t| Gem::Version.new(t.sub(/^v/, "").tr("_", ".")) }
 
-  start_index = releases.index("v#{from_version}") || releases.index(from_version) || releases.index("bundler-v#{from_version}")
-  end_index = releases.index("v#{to_version}") || releases.index(to_version) || releases.index("bundler-v#{to_version}")
+  start_index = releases.index("v#{from_version}") || releases.index(from_version)
+  end_index = releases.index("v#{to_version}") || releases.index(to_version)
   return nil unless start_index && end_index
 
   range = releases[start_index + 1..end_index]
@@ -246,7 +246,7 @@ def collect_gem_updates(versions_from, versions_to)
 
     footnote_links = release_range.map do |rel|
       {
-        ref: "#{name}-#{rel.sub(/^bundler-/, '')}",
+        ref: "#{name}-#{rel}",
         url: "https://github.com/#{org}/#{repo}/releases/tag/#{rel}",
       }
     end
@@ -265,8 +265,7 @@ def collect_gem_updates(versions_from, versions_to)
 
 def format_release_diff(result)
   links = result[:release_range].map do |rel|
-    tag = rel.sub(/^bundler-/, "")
-    "[#{tag}][#{result[:name]}-#{tag}]"
+    "[#{rel}][#{result[:name]}-#{rel}]"
   end
   "  * #{result[:from_version]} to #{links.join(', ')}"
 end
@@ -293,25 +292,20 @@ def update_news_md(results)
   content = File.read(news_path)
   lines = content.lines
 
-  # Build a lookup: gem name => result
-  result_by_name = {}
-  results.each { |r| result_by_name[r[:name]] = r }
+  result_by_name = results.to_h { |r| [r[:name], r] }
 
   new_lines = []
   i = 0
   while i < lines.length
     line = lines[i]
 
-    # Check if this line is a gem bullet like "* gemname x.y.z"
     if line =~ /^\* ([A-Za-z0-9_\-]+)\s+(\d+(?:\.\d+){0,3})\b/
       gem_name = $1
 
       new_lines << line
 
-      if result_by_name.key?(gem_name)
-        r = result_by_name[gem_name]
-
-        # Skip any existing sub-bullet lines that follow (lines starting with spaces + *)
+      if (r = result_by_name[gem_name])
+        # Skip any existing sub-bullet lines that follow
         while i + 1 < lines.length && lines[i + 1] =~ /^\s+\*/
           i += 1
         end

From 9d6deeba3b839b1236f9afd785dfcf8bb12b195a Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 16:04:49 +0900
Subject: [PATCH 07/12] Use the X.Y.0 release as the gem-version baseline

stdgems.org's "X.Y" key tracks the latest 4.0.x patch level, so once a
gem gets bumped in a Ruby patch release the diff baseline shifts forward
and history that should appear in NEWS.md for the next minor disappears.
Prefer the explicit "X.Y.0" key when present so the baseline always
points at the original X.Y.0 release; fall back to "X.Y" or the highest
matching patch otherwise.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 tool/update-NEWS-github-release.rb | 9 ++++++++-
 1 file changed, 8 insertions(+), 1 deletion(-)

diff --git a/tool/update-NEWS-github-release.rb b/tool/update-NEWS-github-release.rb
index 69e58db5f3be05..1957244fcd76ce 100755
--- a/tool/update-NEWS-github-release.rb
+++ b/tool/update-NEWS-github-release.rb
@@ -24,6 +24,11 @@ def fetch_default_gems_versions(ruby_version)
   json = JSON.parse(body)
   gems = json["gems"] || []
 
+  # Prefer the initial release key (e.g. "4.0.0") over the rolling
+  # major.minor key (e.g. "4.0") so the diff baseline reflects the original
+  # X.Y.0 release rather than the latest patch level.
+  initial_release_key = (ruby_version =~ /\A\d+\.\d+\z/) ? "#{ruby_version}.0" : nil
+
   map = {}
   gems.each do |g|
     # Only include default gems (skip ones marked removed)
@@ -38,7 +43,9 @@ def fetch_default_gems_versions(ruby_version)
       category_versions = versions[category] || {}
       next if selected_version
 
-      if category_versions.key?(ruby_version)
+      if initial_release_key && category_versions.key?(initial_release_key)
+        selected_version = category_versions[initial_release_key]
+      elsif category_versions.key?(ruby_version)
         selected_version = category_versions[ruby_version]
       else
         # Fall back to the highest patch version matching the given major.minor

From 6c5f1225a1cc6036732f65e1f43080ddef621eb5 Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 16:13:49 +0900
Subject: [PATCH 08/12] Generate sub-bullets for RubyGems and bundler
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

RubyGems and bundler were skipped outright in collect_gem_updates, so
NEWS.md never picked up the rubygems/rubygems releases shipped between
the X.Y.0 baseline and the in-development X.(Y+1).0.dev. Wire them
through resolve_repo (RubyGems → rubygems/rubygems, bundler same repo
with a "bundler-" tag prefix) and teach fetch_release_range to filter
and look up tags by that prefix. Display tags strip the prefix so the
rendered diff reads "4.0.3 to v4.0.4, ..." for both gems while the
footnote URLs still point at the actual tag names. When the "to"
version ends in .dev/.beta/.rc/etc., the lookup falls back to the
highest released tag so unreleased dev versions still produce a range.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 tool/update-NEWS-github-release.rb | 34 +++++++++++++++++++++---------
 1 file changed, 24 insertions(+), 10 deletions(-)

diff --git a/tool/update-NEWS-github-release.rb b/tool/update-NEWS-github-release.rb
index 1957244fcd76ce..0ef6fcfe377145 100755
--- a/tool/update-NEWS-github-release.rb
+++ b/tool/update-NEWS-github-release.rb
@@ -206,12 +206,16 @@ def resolve_repo(name)
     { repo: name, org: "minitest" }
   when "test-unit"
     { repo: name, org: "test-unit" }
+  when "RubyGems"
+    { repo: "rubygems", org: "rubygems" }
+  when "bundler"
+    { repo: "rubygems", org: "rubygems", tag_prefix: "bundler-" }
   else
     { repo: name, org: "ruby" }
   end
 end
 
-def fetch_release_range(name, from_version, to_version, org, repo)
+def fetch_release_range(name, from_version, to_version, org, repo, tag_prefix: "")
   releases = []
   begin
     Octokit.releases("#{org}/#{repo}").each do |release|
@@ -222,12 +226,18 @@ def fetch_release_range(name, from_version, to_version, org, repo)
     return nil
   end
 
-  # Keep only version-like tags and sort ascending by semantic version
-  releases = releases.select { |t| t =~ /^v\d/ || t =~ /^\d/ }
-  releases = releases.sort_by { |t| Gem::Version.new(t.sub(/^v/, "").tr("_", ".")) }
+  # Keep only this gem's version-like tags and sort ascending by semantic version
+  prefix = Regexp.escape(tag_prefix)
+  releases = releases.select { |t| t =~ /\A#{prefix}v?\d/ }
+  releases = releases.sort_by { |t| Gem::Version.new(t.sub(/\A#{prefix}/, "").sub(/^v/, "").tr("_", ".")) }
+
+  start_index = releases.index("#{tag_prefix}v#{from_version}") || releases.index("#{tag_prefix}#{from_version}")
+  end_index = releases.index("#{tag_prefix}v#{to_version}") || releases.index("#{tag_prefix}#{to_version}")
+
+  # If the "to" version is unreleased (e.g. 4.1.0.dev), include every released
+  # tag after the baseline up to the latest one available.
+  end_index ||= releases.length - 1 if to_version =~ /(?:\.|-)(?:dev|beta|alpha|rc|pre)/i
 
-  start_index = releases.index("v#{from_version}") || releases.index(from_version)
-  end_index = releases.index("v#{to_version}") || releases.index(to_version)
   return nil unless start_index && end_index
 
   range = releases[start_index + 1..end_index]
@@ -242,18 +252,19 @@ def collect_gem_updates(versions_from, versions_to)
   versions_to.each do |name, version|
     # Skip items which do not exist in the FROM map to reduce API calls
     next unless versions_from.key?(name)
-    next if name == "RubyGems" || name == "bundler"
 
     info = resolve_repo(name)
     org = info[:org]
     repo = info[:repo]
+    tag_prefix = info[:tag_prefix] || ""
 
-    release_range = fetch_release_range(name, versions_from[name], version, org, repo)
+    release_range = fetch_release_range(name, versions_from[name], version, org, repo, tag_prefix: tag_prefix)
     next unless release_range
 
     footnote_links = release_range.map do |rel|
+      tag = rel.sub(/\A#{Regexp.escape(tag_prefix)}/, "")
       {
-        ref: "#{name}-#{rel}",
+        ref: "#{name}-#{tag}",
         url: "https://github.com/#{org}/#{repo}/releases/tag/#{rel}",
       }
     end
@@ -264,6 +275,7 @@ def collect_gem_updates(versions_from, versions_to)
       from_version: versions_from[name],
       release_range: release_range,
       footnote_links: footnote_links,
+      tag_prefix: tag_prefix,
     }
   end
 
@@ -271,8 +283,10 @@ def collect_gem_updates(versions_from, versions_to)
 end
 
 def format_release_diff(result)
+  prefix = Regexp.escape(result[:tag_prefix] || "")
   links = result[:release_range].map do |rel|
-    "[#{rel}][#{result[:name]}-#{rel}]"
+    tag = rel.sub(/\A#{prefix}/, "")
+    "[#{tag}][#{result[:name]}-#{tag}]"
   end
   "  * #{result[:from_version]} to #{links.join(', ')}"
 end

From 88f18fde2c0e8bea65fdde8b037c36b5bdafa100 Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 16:32:28 +0900
Subject: [PATCH 09/12] Update with the correct versions from Ruby 4.0.0
 release

---
 NEWS.md | 46 +++++++++++++++++++++++++++++++---------------
 1 file changed, 31 insertions(+), 15 deletions(-)

diff --git a/NEWS.md b/NEWS.md
index f13c16f8ffcc06..fd801103ca43d0 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -68,7 +68,9 @@ releases.
 ### The following default gems are updated.
 
 * RubyGems 4.1.0.dev
+  * 4.0.3 to [v4.0.4][RubyGems-v4.0.4], [v4.0.5][RubyGems-v4.0.5], [v4.0.6][RubyGems-v4.0.6], [v4.0.7][RubyGems-v4.0.7], [v4.0.8][RubyGems-v4.0.8], [v4.0.9][RubyGems-v4.0.9], [v4.0.10][RubyGems-v4.0.10]
 * bundler 4.1.0.dev
+  * 4.0.3 to [v4.0.4][bundler-v4.0.4], [v4.0.5][bundler-v4.0.5], [v4.0.6][bundler-v4.0.6], [v4.0.7][bundler-v4.0.7], [v4.0.8][bundler-v4.0.8], [v4.0.9][bundler-v4.0.9], [v4.0.10][bundler-v4.0.10]
 * erb 6.0.3
   * 6.0.1 to [v6.0.2][erb-v6.0.2], [v6.0.3][erb-v6.0.3]
 * json 2.19.3
@@ -76,12 +78,12 @@ releases.
 * openssl 4.0.1
   * 4.0.0 to [v4.0.1][openssl-v4.0.1]
 * prism 1.9.0
-  * 1.8.1 to [v1.9.0][prism-v1.9.0]
+  * 1.7.0 to [v1.8.0][prism-v1.8.0], [v1.8.1][prism-v1.8.1], [v1.9.0][prism-v1.9.0]
 * resolv 0.7.1
   * 0.7.0 to [v0.7.1][resolv-v0.7.1]
 * stringio 3.2.1.dev
 * strscan 3.1.7.dev
-  * 3.1.6 to [v3.1.7][strscan-v3.1.7]
+  * 3.1.6 to [v3.1.7][strscan-v3.1.7], [v3.1.8][strscan-v3.1.8]
 * syntax_suggest 3.0.0
 * timeout 0.6.1
   * 0.6.0 to [v0.6.1][timeout-v0.6.1]
@@ -98,7 +100,7 @@ releases.
 * net-imap 0.6.3
   * 0.6.2 to [v0.6.3][net-imap-v0.6.3]
 * rbs 4.0.2
-  * 3.10.0 to [v3.10.1][rbs-v3.10.1], [v3.10.2][rbs-v3.10.2], [v3.10.3][rbs-v3.10.3], [v3.10.4][rbs-v3.10.4], [v4.0.0.dev.5][rbs-v4.0.0.dev.5], [v4.0.0][rbs-v4.0.0], [v4.0.2][rbs-v4.0.2]
+  * 3.10.0 to [v3.10.1][rbs-v3.10.1], [v3.10.2][rbs-v3.10.2], [v3.10.3][rbs-v3.10.3], [v3.10.4][rbs-v3.10.4], [v4.0.0.dev.1][rbs-v4.0.0.dev.1], [v4.0.0.dev.2][rbs-v4.0.0.dev.2], [v4.0.0.dev.3][rbs-v4.0.0.dev.3], [v4.0.0.dev.4][rbs-v4.0.0.dev.4], [v4.0.0.dev.5][rbs-v4.0.0.dev.5], [v4.0.0][rbs-v4.0.0], [v4.0.1.dev.1][rbs-v4.0.1.dev.1], [v4.0.1.dev.2][rbs-v4.0.1.dev.2], [v4.0.1][rbs-v4.0.1], [v4.0.2][rbs-v4.0.2]
 * mutex_m 0.3.0
 * bigdecimal 4.1.1
   * 4.0.1 to [v4.1.0][bigdecimal-v4.1.0], [v4.1.1][bigdecimal-v4.1.1]
@@ -164,18 +166,20 @@ A lot of work has gone into making Ractors more stable, performant, and usable.
 [Feature #21853]: https://bugs.ruby-lang.org/issues/21853
 [Feature #21861]: https://bugs.ruby-lang.org/issues/21861
 [Feature #21932]: https://bugs.ruby-lang.org/issues/21932
-[test-unit-3.7.4]: https://github.com/test-unit/test-unit/releases/tag/3.7.4
-[test-unit-3.7.5]: https://github.com/test-unit/test-unit/releases/tag/3.7.5
-[rss-0.3.2]: https://github.com/ruby/rss/releases/tag/0.3.2
-[net-imap-v0.6.2]: https://github.com/ruby/net-imap/releases/tag/v0.6.2
-[debug-v1.11.1]: https://github.com/ruby/debug/releases/tag/v1.11.1
-[rdoc-v7.0.0]: https://github.com/ruby/rdoc/releases/tag/v7.0.0
-[rdoc-v7.0.1]: https://github.com/ruby/rdoc/releases/tag/v7.0.1
-[rdoc-v7.0.2]: https://github.com/ruby/rdoc/releases/tag/v7.0.2
-[rdoc-v7.0.3]: https://github.com/ruby/rdoc/releases/tag/v7.0.3
-[prism-v1.8.1]: https://github.com/ruby/prism/releases/tag/v1.8.1
-[zlib-v3.2.3]: https://github.com/ruby/zlib/releases/tag/v3.2.3
-[pstore-v0.2.1]: https://github.com/ruby/pstore/releases/tag/v0.2.1
+[RubyGems-v4.0.4]: https://github.com/rubygems/rubygems/releases/tag/v4.0.4
+[RubyGems-v4.0.5]: https://github.com/rubygems/rubygems/releases/tag/v4.0.5
+[RubyGems-v4.0.6]: https://github.com/rubygems/rubygems/releases/tag/v4.0.6
+[RubyGems-v4.0.7]: https://github.com/rubygems/rubygems/releases/tag/v4.0.7
+[RubyGems-v4.0.8]: https://github.com/rubygems/rubygems/releases/tag/v4.0.8
+[RubyGems-v4.0.9]: https://github.com/rubygems/rubygems/releases/tag/v4.0.9
+[RubyGems-v4.0.10]: https://github.com/rubygems/rubygems/releases/tag/v4.0.10
+[bundler-v4.0.4]: https://github.com/rubygems/rubygems/releases/tag/bundler-v4.0.4
+[bundler-v4.0.5]: https://github.com/rubygems/rubygems/releases/tag/bundler-v4.0.5
+[bundler-v4.0.6]: https://github.com/rubygems/rubygems/releases/tag/bundler-v4.0.6
+[bundler-v4.0.7]: https://github.com/rubygems/rubygems/releases/tag/bundler-v4.0.7
+[bundler-v4.0.8]: https://github.com/rubygems/rubygems/releases/tag/bundler-v4.0.8
+[bundler-v4.0.9]: https://github.com/rubygems/rubygems/releases/tag/bundler-v4.0.9
+[bundler-v4.0.10]: https://github.com/rubygems/rubygems/releases/tag/bundler-v4.0.10
 [erb-v6.0.2]: https://github.com/ruby/erb/releases/tag/v6.0.2
 [erb-v6.0.3]: https://github.com/ruby/erb/releases/tag/v6.0.3
 [json-v2.18.1]: https://github.com/ruby/json/releases/tag/v2.18.1
@@ -184,10 +188,14 @@ A lot of work has gone into making Ractors more stable, performant, and usable.
 [json-v2.19.2]: https://github.com/ruby/json/releases/tag/v2.19.2
 [json-v2.19.3]: https://github.com/ruby/json/releases/tag/v2.19.3
 [openssl-v4.0.1]: https://github.com/ruby/openssl/releases/tag/v4.0.1
+[prism-v1.8.0]: https://github.com/ruby/prism/releases/tag/v1.8.0
+[prism-v1.8.1]: https://github.com/ruby/prism/releases/tag/v1.8.1
 [prism-v1.9.0]: https://github.com/ruby/prism/releases/tag/v1.9.0
 [resolv-v0.7.1]: https://github.com/ruby/resolv/releases/tag/v0.7.1
 [strscan-v3.1.7]: https://github.com/ruby/strscan/releases/tag/v3.1.7
+[strscan-v3.1.8]: https://github.com/ruby/strscan/releases/tag/v3.1.8
 [timeout-v0.6.1]: https://github.com/ruby/timeout/releases/tag/v0.6.1
+[zlib-v3.2.3]: https://github.com/ruby/zlib/releases/tag/v3.2.3
 [rake-v13.4.0]: https://github.com/ruby/rake/releases/tag/v13.4.0
 [rake-v13.4.1]: https://github.com/ruby/rake/releases/tag/v13.4.1
 [rake-v13.4.2]: https://github.com/ruby/rake/releases/tag/v13.4.2
@@ -198,8 +206,15 @@ A lot of work has gone into making Ractors more stable, performant, and usable.
 [rbs-v3.10.2]: https://github.com/ruby/rbs/releases/tag/v3.10.2
 [rbs-v3.10.3]: https://github.com/ruby/rbs/releases/tag/v3.10.3
 [rbs-v3.10.4]: https://github.com/ruby/rbs/releases/tag/v3.10.4
+[rbs-v4.0.0.dev.1]: https://github.com/ruby/rbs/releases/tag/v4.0.0.dev.1
+[rbs-v4.0.0.dev.2]: https://github.com/ruby/rbs/releases/tag/v4.0.0.dev.2
+[rbs-v4.0.0.dev.3]: https://github.com/ruby/rbs/releases/tag/v4.0.0.dev.3
+[rbs-v4.0.0.dev.4]: https://github.com/ruby/rbs/releases/tag/v4.0.0.dev.4
 [rbs-v4.0.0.dev.5]: https://github.com/ruby/rbs/releases/tag/v4.0.0.dev.5
 [rbs-v4.0.0]: https://github.com/ruby/rbs/releases/tag/v4.0.0
+[rbs-v4.0.1.dev.1]: https://github.com/ruby/rbs/releases/tag/v4.0.1.dev.1
+[rbs-v4.0.1.dev.2]: https://github.com/ruby/rbs/releases/tag/v4.0.1.dev.2
+[rbs-v4.0.1]: https://github.com/ruby/rbs/releases/tag/v4.0.1
 [rbs-v4.0.2]: https://github.com/ruby/rbs/releases/tag/v4.0.2
 [bigdecimal-v4.1.0]: https://github.com/ruby/bigdecimal/releases/tag/v4.1.0
 [bigdecimal-v4.1.1]: https://github.com/ruby/bigdecimal/releases/tag/v4.1.1
@@ -208,6 +223,7 @@ A lot of work has gone into making Ractors more stable, performant, and usable.
 [repl_type_completor-v0.1.13]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.13
 [repl_type_completor-v0.1.14]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.14
 [repl_type_completor-v0.1.15]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.15
+[pstore-v0.2.1]: https://github.com/ruby/pstore/releases/tag/v0.2.1
 [rdoc-v7.1.0]: https://github.com/ruby/rdoc/releases/tag/v7.1.0
 [rdoc-v7.2.0]: https://github.com/ruby/rdoc/releases/tag/v7.2.0
 [win32ole-v1.9.3]: https://github.com/ruby/win32ole/releases/tag/v1.9.3

From 509b0e4dc3a21b88cdb76526b6c68452eaf36853 Mon Sep 17 00:00:00 2001
From: Hiroshi SHIBATA <hsbt@ruby-lang.org>
Date: Fri, 17 Apr 2026 16:34:34 +0900
Subject: [PATCH 10/12] Fixed the wrong dev version of strscan

---
 NEWS.md               | 2 +-
 ext/strscan/strscan.c | 2 +-
 2 files changed, 2 insertions(+), 2 deletions(-)

diff --git a/NEWS.md b/NEWS.md
index fd801103ca43d0..749e28cf9d423a 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -82,7 +82,7 @@ releases.
 * resolv 0.7.1
   * 0.7.0 to [v0.7.1][resolv-v0.7.1]
 * stringio 3.2.1.dev
-* strscan 3.1.7.dev
+* strscan 3.1.9.dev
   * 3.1.6 to [v3.1.7][strscan-v3.1.7], [v3.1.8][strscan-v3.1.8]
 * syntax_suggest 3.0.0
 * timeout 0.6.1
diff --git a/ext/strscan/strscan.c b/ext/strscan/strscan.c
index 7efee0b5db4d1e..0f20889dc326a1 100644
--- a/ext/strscan/strscan.c
+++ b/ext/strscan/strscan.c
@@ -22,7 +22,7 @@ extern size_t onig_region_memsize(const struct re_registers *regs);
 
 #include <stdbool.h>
 
-#define STRSCAN_VERSION "3.1.7.dev"
+#define STRSCAN_VERSION "3.1.9.dev"
 
 
 #ifdef HAVE_RB_DEPRECATE_CONSTANT

From 27af8317b9045338d3794f5c4b169a6bf5262c1a Mon Sep 17 00:00:00 2001
From: Benoit Daloze <eregontp@gmail.com>
Date: Fri, 17 Apr 2026 12:00:54 +0200
Subject: [PATCH 11/12] Fix timeout_scale= call to use the correct receiver

* See https://github.com/ruby/test-unit-ruby-core/pull/23
---
 tool/lib/envutil.rb | 16 ++++++++--------
 1 file changed, 8 insertions(+), 8 deletions(-)

diff --git a/tool/lib/envutil.rb b/tool/lib/envutil.rb
index dcc9148a8407f0..b4c7d1d03564fd 100644
--- a/tool/lib/envutil.rb
+++ b/tool/lib/envutil.rb
@@ -48,14 +48,6 @@ class << self
     attr_reader :original_internal_encoding, :original_external_encoding,
                 :original_verbose, :original_warning
 
-    if RUBY_ENGINE == "truffleruby"
-      # Tests relying on timeout have high variance on TruffleRuby due to the highly-optimizing JIT, deoptimization, profiling interpreter, different GC, etc.
-      # Setting a default timeout scale helps avoid transient failures for tests relying on timeouts.
-      # We choose 10 because it is the same number used in CRuby CI on macOS:
-      # https://github.com/ruby/ruby/blob/9d46b0c735877f152a0b4b16b8153c6f395dee28/.github/workflows/macos.yml#L133
-      self.timeout_scale = 10
-    end
-
     def capture_global_values
       @original_internal_encoding = Encoding.default_internal
       @original_external_encoding = Encoding.default_external
@@ -71,6 +63,14 @@ def capture_global_values
     end
   end
 
+  if RUBY_ENGINE == "truffleruby"
+    # Tests relying on timeout have high variance on TruffleRuby due to the highly-optimizing JIT, deoptimization, profiling interpreter, different GC, etc.
+    # Setting a default timeout scale helps avoid transient failures for tests relying on timeouts.
+    # We choose 10 because it is the same number used in CRuby CI on macOS:
+    # https://github.com/ruby/ruby/blob/9d46b0c735877f152a0b4b16b8153c6f395dee28/.github/workflows/macos.yml#L133
+    self.timeout_scale = 10
+  end
+
   def apply_timeout_scale(t)
     if scale = EnvUtil.timeout_scale
       t * scale

From 11e3c78b61da705c783dd12fb7f158c0d256ede0 Mon Sep 17 00:00:00 2001
From: Nick Dower <nicholasdower@gmail.com>
Date: Sat, 11 Apr 2026 14:08:40 +0200
Subject: [PATCH 12/12] [ruby/rubygems] Fix installing gems with native
 extensions + transitive dependencies

I am seeing the following error during bundle install:

```
Gem::MissingSpecError: Could not find 'ffi' (>= 1.15.5) among 48 total gem(s) (Gem::MissingSpecError)
```

This is reproducible with:

```ruby
source 'https://rubygems.org'

gem 'llhttp-ffi'
```

It seems only direct dependencies are checked when determining whether
a Gem with native extensions is ready to install. I believe this can
lead to a failure if a transitive dependency is not yet installed.

In the example above, llhttp-ffi depends on ffi-compiler, which depends
on ffi.  Since ffi-compiler has no extensions, it is installed
immediately without waiting for ffi. When llhttp-ffi then checks its
direct dependencies, ffi-compiler is already installed, so llhttp-ffi
starts building its native extension. The build requires ffi, which may
not have been installed yet.

https://github.com/ruby/rubygems/commit/a1f5751177
---
 lib/bundler/installer/parallel_installer.rb   | 30 +++----
 .../installer/spec_installation_spec.rb       | 79 ++++++++++++-------
 spec/bundler/commands/install_spec.rb         | 42 ++++++++++
 3 files changed, 103 insertions(+), 48 deletions(-)

diff --git a/lib/bundler/installer/parallel_installer.rb b/lib/bundler/installer/parallel_installer.rb
index 020db30b8443b5..fef326ed0a9c8a 100644
--- a/lib/bundler/installer/parallel_installer.rb
+++ b/lib/bundler/installer/parallel_installer.rb
@@ -6,7 +6,7 @@
 module Bundler
   class ParallelInstaller
     class SpecInstallation
-      attr_accessor :spec, :name, :full_name, :post_install_message, :state, :error
+      attr_accessor :spec, :name, :full_name, :post_install_message, :state, :error, :dependencies
       def initialize(spec)
         @spec = spec
         @name = spec.name
@@ -46,25 +46,11 @@ def has_post_install_message?
         !post_install_message.empty?
       end
 
-      def ignorable_dependency?(dep)
-        dep.type == :development || dep.name == @name
-      end
-
-      # Checks installed dependencies against spec's dependencies to make
-      # sure needed dependencies have been installed.
+      # Recursively checks that all dependencies (direct and transitive) have been installed.
       def dependencies_installed?(installed_specs)
-        dependencies.all? {|d| installed_specs.include? d.name }
-      end
-
-      # Represents only the non-development dependencies, the ones that are
-      # itself and are in the total list.
-      def dependencies
-        @dependencies ||= all_dependencies.reject {|dep| ignorable_dependency? dep }
-      end
-
-      # Represents all dependencies
-      def all_dependencies
-        @spec.dependencies
+        dependencies.all? do |dep|
+          installed_specs.include?(dep.name) && dep.dependencies_installed?(installed_specs)
+        end
       end
 
       def to_s
@@ -85,6 +71,12 @@ def initialize(installer, all_specs, size, standalone, force, local: false, skip
       @force = force
       @local = local
       @specs = all_specs.map {|s| SpecInstallation.new(s) }
+      specs_by_name = @specs.to_h {|s| [s.name, s] }
+      @specs.each do |spec_install|
+        spec_install.dependencies = spec_install.spec.dependencies.filter_map do |dep|
+          specs_by_name[dep.name] unless dep.type == :development || dep.name == spec_install.name
+        end
+      end
       @specs.each do |spec_install|
         spec_install.state = :installed if skip.include?(spec_install.name)
       end if skip
diff --git a/spec/bundler/bundler/installer/spec_installation_spec.rb b/spec/bundler/bundler/installer/spec_installation_spec.rb
index cbe2589b99b740..57868766d9b37a 100644
--- a/spec/bundler/bundler/installer/spec_installation_spec.rb
+++ b/spec/bundler/bundler/installer/spec_installation_spec.rb
@@ -3,18 +3,17 @@
 require "bundler/installer/parallel_installer"
 
 RSpec.describe Bundler::ParallelInstaller::SpecInstallation do
-  let!(:dep) do
-    a_spec = Object.new
-    def a_spec.name
-      "I like tests"
-    end
-
-    def a_spec.full_name
-      "I really like tests"
-    end
-    a_spec
+  def build_spec(name, extensions: [])
+    spec = Object.new
+    spec.define_singleton_method(:name) { name }
+    spec.define_singleton_method(:full_name) { "#{name}-1.0" }
+    spec.define_singleton_method(:extensions) { extensions }
+    spec.define_singleton_method(:dependencies) { [] }
+    spec
   end
 
+  let!(:dep) { build_spec("I like tests") }
+
   describe "#ready_to_enqueue?" do
     context "when in enqueued state" do
       it "is falsey" do
@@ -39,29 +38,51 @@ def a_spec.full_name
   end
 
   describe "#dependencies_installed?" do
-    context "when all dependencies are installed" do
-      it "returns true" do
-        dependencies = []
-        dependencies << instance_double("SpecInstallation", spec: "alpha", name: "alpha", installed?: true, all_dependencies: [], type: :production)
-        dependencies << instance_double("SpecInstallation", spec: "beta", name: "beta", installed?: true, all_dependencies: [], type: :production)
-        all_specs = dependencies + [instance_double("SpecInstallation", spec: "gamma", name: "gamma", installed?: false, all_dependencies: [], type: :production)]
+    it "returns true when all dependencies are installed" do
+      alpha = described_class.new(build_spec("alpha"))
+      alpha.dependencies = []
+
+      beta = described_class.new(build_spec("beta"))
+      beta.dependencies = [alpha]
+
+      gamma = described_class.new(build_spec("gamma"))
+      gamma.dependencies = [beta]
+
+      expect(gamma.dependencies_installed?({})).to be_falsey
+      expect(gamma.dependencies_installed?({ "beta" => true })).to be_falsey
+      expect(gamma.dependencies_installed?({ "alpha" => true, "beta" => true })).to be_truthy
+    end
+  end
+
+  describe "#ready_to_install?" do
+    context "when spec has no extensions" do
+      it "returns true regardless of dependencies" do
+        beta = described_class.new(build_spec("beta"))
+        beta.dependencies = []
+
         spec = described_class.new(dep)
-        allow(spec).to receive(:all_dependencies).and_return(dependencies)
-        installed_specs = all_specs.select(&:installed?).map {|s| [s.name, true] }.to_h
-        expect(spec.dependencies_installed?(installed_specs)).to be_truthy
+        spec.state = :downloaded
+        spec.dependencies = [beta]
+
+        expect(spec.ready_to_install?({})).to be_truthy
       end
     end
 
-    context "when all dependencies are not installed" do
-      it "returns false" do
-        dependencies = []
-        dependencies << instance_double("SpecInstallation", spec: "alpha", name: "alpha", installed?: false, all_dependencies: [], type: :production)
-        dependencies << instance_double("SpecInstallation", spec: "beta", name: "beta", installed?: true, all_dependencies: [], type: :production)
-        all_specs = dependencies + [instance_double("SpecInstallation", spec: "gamma", name: "gamma", installed?: false, all_dependencies: [], type: :production)]
-        spec = described_class.new(dep)
-        allow(spec).to receive(:all_dependencies).and_return(dependencies)
-        installed_specs = all_specs.select(&:installed?).map {|s| [s.name, true] }.to_h
-        expect(spec.dependencies_installed?(installed_specs)).to be_falsey
+    context "when spec has extensions" do
+      it "returns true when all dependencies are installed" do
+        alpha = described_class.new(build_spec("alpha"))
+        alpha.dependencies = []
+
+        beta = described_class.new(build_spec("beta"))
+        beta.dependencies = [alpha]
+
+        gamma = described_class.new(build_spec("gamma", extensions: ["ext/Rakefile"]))
+        gamma.state = :downloaded
+        gamma.dependencies = [beta]
+
+        expect(gamma.ready_to_install?({})).to be_falsey
+        expect(gamma.ready_to_install?({ "beta" => true })).to be_falsey
+        expect(gamma.ready_to_install?({ "alpha" => true, "beta" => true })).to be_truthy
       end
     end
   end
diff --git a/spec/bundler/commands/install_spec.rb b/spec/bundler/commands/install_spec.rb
index bb9b2b1f98a500..8dedeb7d0776aa 100644
--- a/spec/bundler/commands/install_spec.rb
+++ b/spec/bundler/commands/install_spec.rb
@@ -1379,6 +1379,48 @@ def run
     end
   end
 
+  describe "when a native extension requires a transitive dependency at build time" do
+    before do
+      build_repo4 do
+        build_gem "alpha", "1.0.0" do |s|
+          extension = "ext/alpha/extconf.rb"
+          s.extensions = extension
+          s.write(extension, <<~CODE)
+            require "mkmf"
+            sleep 1
+            create_makefile("alpha")
+          CODE
+          s.write "lib/alpha.rb", "ALPHA = '1.0.0'"
+        end
+
+        build_gem "beta", "1.0.0" do |s|
+          s.add_dependency "alpha"
+          s.write "lib/beta.rb", "require 'alpha'\nBETA = '1.0.0'"
+        end
+
+        build_gem "gamma", "1.0.0" do |s|
+          s.add_dependency "beta"
+          extension = "ext/gamma/extconf.rb"
+          s.extensions = extension
+          s.write(extension, <<~EXTCONF)
+            require "beta"
+            require "mkmf"
+            create_makefile("gamma")
+          EXTCONF
+        end
+      end
+    end
+
+    it "installs successfully" do
+      install_gemfile <<~G
+        source "https://gem.repo4"
+        gem "gamma"
+      G
+
+      expect(the_bundle).to include_gems "alpha 1.0.0", "beta 1.0.0", "gamma 1.0.0"
+    end
+  end
+
   describe "when configured path is UTF-8 and a file inside a gem package too" do
     let(:app_path) do
       path = tmp("♥")