diff --git a/lib/bundler/match_platform.rb b/lib/bundler/match_platform.rb
index 566067c905a0..fab1910be01b 100644
--- a/lib/bundler/match_platform.rb
+++ b/lib/bundler/match_platform.rb
@@ -31,11 +31,21 @@ def self.prefer_content_addressable(matching)
       return matching if addressable.empty?
 
       compatible = addressable.select(&:matches_current_metadata?)
+      compatible.reject! {|spec| longer_matching_content_address_available?(spec, compatible) }
       return compatible if compatible.any?
 
       non_addressable.any? ? non_addressable : matching
     end
 
+    def self.longer_matching_content_address_available?(spec, compatible_specs)
+      compatible_specs.any? do |compatible_spec|
+        compatible_spec.platform == spec.platform &&
+          compatible_spec.content_address.length > spec.content_address.length &&
+          compatible_spec.content_address.start_with?(spec.content_address)
+      end
+    end
+    private_class_method :longer_matching_content_address_available?
+
     def self.select_best_local_platform_match(specs, force_ruby: false, locked_platforms: nil)
       local = Bundler.local_platform
       matching = select_all_platform_match(specs, local, force_ruby: force_ruby)
diff --git a/lib/rubygems/content_address.rb b/lib/rubygems/content_address.rb
index e815c45191c0..bed6a763d0c1 100644
--- a/lib/rubygems/content_address.rb
+++ b/lib/rubygems/content_address.rb
@@ -34,6 +34,13 @@ def self.match?(value)
     value.is_a?(String) && PATTERN.match?(value)
   end
 
+  ##
+  # Whether +value+ is a valid content address longer than the default.
+
+  def self.widened?(value)
+    match?(value) && value.length > DEFAULT_LENGTH
+  end
+
   ##
   # Whether +value+ is a well-formed Ruby ABI ("X.Y").
 
diff --git a/lib/rubygems/resolver.rb b/lib/rubygems/resolver.rb
index ffe0e9f60785..c0b5ea1df0ca 100644
--- a/lib/rubygems/resolver.rb
+++ b/lib/rubygems/resolver.rb
@@ -477,10 +477,19 @@ def build_spec_for_cache(name)
     @all_specs[name].group_by(&:version).transform_values do |candidates|
       next candidates.first if candidates.length == 1
 
-      # Prefer already-installed specs to avoid unnecessary downloads
+      # Prefer already-installed specs to avoid unnecessary downloads.
       installed = candidates.select {|s| s.is_a?(Gem::Resolver::InstalledSpecification) }
-      next installed.first if installed.length == 1
-      candidates = installed if installed.any?
+
+      superseded_installed = installed.select do |installed_spec|
+        candidates.any? {|candidate| widened_remote_spec_supersedes?(candidate, installed_spec) }
+      end
+
+      if superseded_installed.any?
+        candidates -= superseded_installed
+      else
+        next installed.first if installed.length == 1
+        candidates = installed if installed.any?
+      end
 
       # Among remaining candidates, prefer a content-addressed candidate
       # built for the running Ruby, then the most specific platform, then the
@@ -496,6 +505,22 @@ def build_spec_for_cache(name)
     end
   end
 
+  def widened_remote_spec_supersedes?(candidate, installed_spec)
+    return false if candidate.is_a?(Gem::Resolver::InstalledSpecification)
+
+    candidate_address = candidate.content_address
+    installed_address = installed_spec.content_address
+
+    return false unless Gem::ContentAddress.match?(candidate_address)
+    return false unless installed_address&.length == Gem::ContentAddress::DEFAULT_LENGTH
+    return false unless candidate_address.length > installed_address.length
+
+    candidate.platform == installed_spec.platform &&
+      Gem::ContentAddress.ruby_abi_for(candidate.required_ruby_version) ==
+        Gem::ContentAddress.ruby_abi_for(installed_spec.required_ruby_version) &&
+      candidate_address.start_with?(installed_address)
+  end
+
   def compute_dependencies(package, version)
     spec = spec_for(package.to_s, version)
     return {} unless spec
diff --git a/spec/bundler/match_platform_spec.rb b/spec/bundler/match_platform_spec.rb
new file mode 100644
index 000000000000..24f77ebf66b4
--- /dev/null
+++ b/spec/bundler/match_platform_spec.rb
@@ -0,0 +1,44 @@
+# frozen_string_literal: true
+
+RSpec.describe Bundler::MatchPlatform do
+  describe ".prefer_content_addressable" do
+    it "prefers a widened address when its platform and prefix match" do
+      platform = Gem::Platform.new("arm64-darwin")
+      short = double(
+        :short,
+        platform: platform,
+        content_address: "ab123456",
+        matches_current_metadata?: true
+      )
+      widened = double(
+        :widened,
+        platform: platform,
+        content_address: "ab1234567890",
+        matches_current_metadata?: true
+      )
+
+      matching = described_class.prefer_content_addressable([short, widened])
+
+      expect(matching).to contain_exactly(widened)
+    end
+
+    it "does not replace a short address when the widened address has a different platform" do
+      short = double(
+        :short,
+        platform: Gem::Platform.new("arm64-darwin-27"),
+        content_address: "ab123456",
+        matches_current_metadata?: true
+      )
+      widened = double(
+        :widened,
+        platform: Gem::Platform.new("arm64-darwin"),
+        content_address: "ab1234567890",
+        matches_current_metadata?: true
+      )
+
+      matching = described_class.prefer_content_addressable([short, widened])
+
+      expect(matching).to contain_exactly(short, widened)
+    end
+  end
+end
diff --git a/spec/install/gemfile/content_addressable_spec.rb b/spec/install/gemfile/content_addressable_spec.rb
index 8493c89cc203..1363ddd32603 100644
--- a/spec/install/gemfile/content_addressable_spec.rb
+++ b/spec/install/gemfile/content_addressable_spec.rb
@@ -56,6 +56,50 @@
     end
   end
 
+  it "prefers a widened server address over an installed short address" do
+    simulate_platform "x86_64-linux" do
+      build_repo2 do
+        build_gem "mygem", "1.0" do |s|
+          s.platform = Gem::Platform.new("x86_64-linux")
+          s.write "lib/mygem.rb", "MYGEM = '1.0 not_content_addressed'"
+        end
+      end
+
+      build_gem "mygem", "1.0", ruby_abi: current_abi, path: gem_repo2("gems") do |s|
+        s.platform = Gem::Platform.new("x86_64-linux")
+        s.required_ruby_version = "~> #{current_abi}.0"
+        s.write "lib/mygem.rb", "MYGEM = '1.0 content_addressed'"
+      end
+
+      install_gemfile <<~G, artifice: "compact_index_v2", env: { "BUNDLER_SPEC_GEM_REPO" => gem_repo2.to_s }
+        source "https://gem.repo2"
+
+        gem "mygem"
+      G
+
+      short_cache = Dir[default_bundle_path("cache", "mygem-1.0-*.gem").to_s].first
+      short_address = File.basename(short_cache, ".gem").rpartition("-").last
+      expect(short_address.length).to eq(Gem::ContentAddress::DEFAULT_LENGTH)
+
+      digest = Digest::SHA256.file(short_cache).hexdigest
+      widened_address = digest[0, 12]
+      short_repo_gem = gem_repo2("gems", "mygem-1.0-#{short_address}.gem")
+      widened_repo_gem = gem_repo2("gems", "mygem-1.0-#{widened_address}.gem")
+
+      update_repo2 do
+        FileUtils.mv short_repo_gem, widened_repo_gem
+      end
+
+      bundle "update mygem", artifice: "compact_index_v2", env: { "BUNDLER_SPEC_GEM_REPO" => gem_repo2.to_s }
+
+      expect(lockfile).to include("mygem (1.0-x86_64-linux) #{widened_address}")
+      expect(default_bundle_path("gems", "mygem-1.0-#{widened_address}")).to exist
+      expect(default_bundle_path("specifications", current_abi, "mygem-1.0-#{widened_address}.gemspec")).to exist
+      expect(default_bundle_path("cache", "mygem-1.0-#{widened_address}.gem")).to exist
+      expect(lockfile).not_to match(/mygem \(1\.0-x86_64-linux\) #{short_address}\s/)
+    end
+  end
+
   it "resolves a content-addressed binary from the local cache after a lockfile round-trip" do
     simulate_platform "x86_64-linux" do
       build_repo2 do
diff --git a/spec/support/shards.rb b/spec/support/shards.rb
index 93e1ccb99462..983b56ccfa71 100644
--- a/spec/support/shards.rb
+++ b/spec/support/shards.rb
@@ -144,6 +144,7 @@ module Shards
         "spec/bundler/ci_detector_spec.rb",
       ],
       shard_d: [
+        "spec/bundler/match_platform_spec.rb",
         "spec/bundler/cli/exec_spec.rb",
         "spec/bundler/rubygems_ext_spec.rb",
         "spec/bundler/resolver/cooldown_spec.rb",
diff --git a/test/rubygems/test_gem_content_address.rb b/test/rubygems/test_gem_content_address.rb
index 868d4ad6866d..775b3232e69c 100644
--- a/test/rubygems/test_gem_content_address.rb
+++ b/test/rubygems/test_gem_content_address.rb
@@ -26,6 +26,13 @@ def test_match_rejects_uppercase
     refute Gem::ContentAddress.match?("ABCDEF12")
   end
 
+  def test_widened
+    refute Gem::ContentAddress.widened?("a" * 8)
+    assert Gem::ContentAddress.widened?("a" * 9)
+    refute Gem::ContentAddress.widened?(nil)
+    refute Gem::ContentAddress.widened?("not-an-address")
+  end
+
   def test_valid_ruby_abi
     assert Gem::ContentAddress.valid_ruby_abi?("3.4")
     assert Gem::ContentAddress.valid_ruby_abi?("10.0")
diff --git a/test/rubygems/test_gem_resolver.rb b/test/rubygems/test_gem_resolver.rb
index 9fff107e02d3..5ae71353e082 100644
--- a/test/rubygems/test_gem_resolver.rb
+++ b/test/rubygems/test_gem_resolver.rb
@@ -336,6 +336,108 @@ def test_prefers_content_addressed_gem_for_same_platform
     assert_resolves_to [ca_spec], resolver
   end
 
+  def test_prefers_remote_gem_with_widened_address_when_first_8_chars_match
+    current_abi = Gem.ruby_abi
+    util_pin_ruby_to_abi current_abi
+    installed_set = Gem::Resolver::CurrentSet.new
+    ca_spec = util_spec "a", "1"
+    ca_spec.platform = Gem::Platform.local
+    ca_spec.content_address = "ab123456"
+    ca_spec.required_ruby_version = "~> #{current_abi}.0"
+    ca_installed_spec = Gem::Resolver::InstalledSpecification.new installed_set, ca_spec
+
+    # Add another installed spec for a different platform
+    # to confirm that this gem is preserved and not accidentally replaced by a widened remote spec.
+    other_platform_spec = util_spec "a", "1"
+    other_platform_spec.platform = "arm64-darwin"
+    other_platform_spec.content_address = "ab123456"
+    other_platform_spec.required_ruby_version = "~> #{current_abi}.0"
+    other_platform_installed_spec = Gem::Resolver::InstalledSpecification.new installed_set, other_platform_spec
+
+    api_set = Gem::Resolver::APISet.new
+    data = {
+      name: "a",
+      number: "1",
+      suffix: "ab1234567890",
+      dependencies: [],
+      requirements: { platform: [Gem::Platform.local.to_s], ruby: ["~> #{current_abi}.0"] },
+    }
+    widened_api_spec = Gem::Resolver::APISpecification.new api_set, data
+
+    s = StaticSet.new([ca_installed_spec, other_platform_installed_spec, widened_api_spec])
+    dependency = make_dep "a"
+    resolver = Gem::Resolver.new([dependency], s)
+    resolved_spec = resolver.resolve.first.spec
+
+    assert_same widened_api_spec, resolved_spec
+    assert_equal "ab1234567890", resolved_spec.content_address
+  ensure
+    util_restore_RUBY_VERSION
+  end
+
+  def test_does_not_replace_installed_gem_with_widened_address_for_different_ruby_abi
+    current_abi = Gem.ruby_abi
+    util_pin_ruby_to_abi current_abi
+    other_abi = current_abi == "2.7" ? "3.0" : "2.7"
+    installed_set = Gem::Resolver::CurrentSet.new
+    ca_spec = util_spec "a", "1"
+    ca_spec.platform = Gem::Platform.local
+    ca_spec.content_address = "ab123456"
+    ca_spec.required_ruby_version = "~> #{current_abi}.0"
+    ca_installed_spec = Gem::Resolver::InstalledSpecification.new installed_set, ca_spec
+
+    api_set = Gem::Resolver::APISet.new
+    data = {
+      name: "a",
+      number: "1",
+      suffix: "ab1234567890",
+      dependencies: [],
+      requirements: { platform: [Gem::Platform.local.to_s], ruby: ["~> #{other_abi}.0"] },
+    }
+    widened_api_spec = Gem::Resolver::APISpecification.new api_set, data
+
+    s = StaticSet.new([ca_installed_spec, widened_api_spec])
+    dependency = make_dep "a"
+    resolver = Gem::Resolver.new([dependency], s)
+    resolver.soft_missing = true
+    resolved_spec = resolver.resolve.first.spec
+
+    assert_same ca_installed_spec, resolved_spec
+  ensure
+    util_restore_RUBY_VERSION
+  end
+
+  def test_does_not_replace_installed_gem_with_widened_address_for_different_platform
+    util_set_arch "arm64-darwin-27"
+    current_abi = Gem.ruby_abi
+    util_pin_ruby_to_abi current_abi
+    installed_set = Gem::Resolver::CurrentSet.new
+    ca_spec = util_spec "a", "1"
+    ca_spec.platform = Gem::Platform.local
+    ca_spec.content_address = "ab123456"
+    ca_spec.required_ruby_version = "~> #{current_abi}.0"
+    ca_installed_spec = Gem::Resolver::InstalledSpecification.new installed_set, ca_spec
+
+    api_set = Gem::Resolver::APISet.new
+    data = {
+      name: "a",
+      number: "1",
+      suffix: "ab1234567890",
+      dependencies: [],
+      requirements: { platform: ["= arm64-darwin"], ruby: ["~> #{current_abi}.0"] },
+    }
+    widened_api_spec = Gem::Resolver::APISpecification.new api_set, data
+
+    s = StaticSet.new([ca_installed_spec, widened_api_spec])
+    dependency = make_dep "a"
+    resolver = Gem::Resolver.new([dependency], s)
+    resolved_spec = resolver.resolve.first.spec
+
+    assert_same ca_installed_spec, resolved_spec
+  ensure
+    util_restore_RUBY_VERSION
+  end
+
   def test_prefers_compatible_content_addressed_gem_over_more_specific_platform
     util_set_arch "arm64-darwin-27"
     current_abi = Gem.ruby_abi