diff --git a/Library/Homebrew/dependency.rb b/Library/Homebrew/dependency.rb
index 30189a48fef27..5d6c0173da9d0 100644
--- a/Library/Homebrew/dependency.rb
+++ b/Library/Homebrew/dependency.rb
@@ -43,10 +43,15 @@ def to_formula(prefer_stub: false)
   end
 
   sig {
-    params(minimum_version: T.nilable(Version), minimum_revision: T.nilable(Integer),
-           minimum_compatibility_version: T.nilable(Integer)).returns(T::Boolean)
+    params(
+      minimum_version:               T.nilable(Version),
+      minimum_revision:              T.nilable(Integer),
+      minimum_compatibility_version: T.nilable(Integer),
+      bottle_os_version:             T.nilable(String),
+    ).returns(T::Boolean)
   }
-  def installed?(minimum_version: nil, minimum_revision: nil, minimum_compatibility_version: nil)
+  def installed?(minimum_version: nil, minimum_revision: nil, minimum_compatibility_version: nil,
+                 bottle_os_version: nil)
     formula = begin
       to_formula(prefer_stub: true)
     rescue FormulaUnavailableError
@@ -95,8 +100,8 @@ def installed?(minimum_version: nil, minimum_revision: nil, minimum_compatibilit
   end
 
   def satisfied?(inherited_options = [], minimum_version: nil, minimum_revision: nil,
-                 minimum_compatibility_version: nil)
-    installed?(minimum_version:, minimum_revision:, minimum_compatibility_version:) &&
+                 minimum_compatibility_version: nil, bottle_os_version: nil)
+    installed?(minimum_version:, minimum_revision:, minimum_compatibility_version:, bottle_os_version:) &&
       missing_options(inherited_options).empty?
   end
 
@@ -277,25 +282,39 @@ def hash
   end
 
   sig {
-    params(minimum_version: T.nilable(Version), minimum_revision: T.nilable(Integer),
-           minimum_compatibility_version: T.nilable(Integer)).returns(T::Boolean)
+    params(
+      minimum_version:               T.nilable(Version),
+      minimum_revision:              T.nilable(Integer),
+      minimum_compatibility_version: T.nilable(Integer),
+      bottle_os_version:             T.nilable(String),
+    ).returns(T::Boolean)
   }
-  def installed?(minimum_version: nil, minimum_revision: nil, minimum_compatibility_version: nil)
-    use_macos_install? || super
+  def installed?(minimum_version: nil, minimum_revision: nil, minimum_compatibility_version: nil,
+                 bottle_os_version: nil)
+    use_macos_install?(bottle_os_version:) || super
   end
 
-  sig { returns(T::Boolean) }
-  def use_macos_install?
+  sig { params(bottle_os_version: T.nilable(String)).returns(T::Boolean) }
+  def use_macos_install?(bottle_os_version: nil)
     # Check whether macOS is new enough for dependency to not be required.
     if Homebrew::SimulateSystem.simulating_or_running_on_macos?
-      # Assume the oldest macOS version when simulating a generic macOS version
-      return true if Homebrew::SimulateSystem.current_os == :macos && !bounds.key?(:since)
-
-      if Homebrew::SimulateSystem.current_os != :macos
-        current_os = MacOSVersion.from_symbol(Homebrew::SimulateSystem.current_os)
-        since_os = MacOSVersion.from_symbol(bounds[:since]) if bounds.key?(:since)
-        return true if current_os >= since_os
+      # If there's no since bound, the dependency is always available from macOS
+      since_os_bounds = bounds[:since]
+      return true if since_os_bounds.blank?
+
+      # When installing a bottle built on an older macOS version, use that version
+      # to determine if the dependency should come from macOS or Homebrew
+      effective_os = if bottle_os_version.present? &&
+                        bottle_os_version.start_with?("macOS ")
+        # bottle_os_version is a string like "14" for Sonoma, "15" for Sequoia
+        # Convert it to a MacOS version symbol for comparison
+        MacOSVersion.new(bottle_os_version.delete_prefix("macOS "))
+      else
+        MacOSVersion.from_symbol(Homebrew::SimulateSystem.current_os)
       end
+
+      since_os = MacOSVersion.from_symbol(since_os_bounds)
+      return true if effective_os >= since_os
     end
 
     false
diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index 305f51c55f42f..3e99e5a21e02a 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -138,6 +138,7 @@ def initialize(
     @poured_bottle = T.let(false, T::Boolean)
     @start_time = T.let(nil, T.nilable(Time))
     @bottle_tab_runtime_dependencies = T.let({}.freeze, T::Hash[String, T::Hash[String, String]])
+    @bottle_built_os_version = T.let(nil, T.nilable(String))
     @hold_locks = T.let(false, T::Boolean)
     @show_summary_heading = T.let(false, T::Boolean)
     @etc_var_preinstall = T.let([], T::Array[Pathname])
@@ -338,12 +339,22 @@ def prelude
 
     Tab.clear_cache
 
-    # Setup bottle_tab_runtime_dependencies for compute_dependencies
+    # Setup bottle_tab_runtime_dependencies for compute_dependencies and
+    # bottle_built_os_version for dependency resolution.
     begin
-      @bottle_tab_runtime_dependencies = formula.bottle_tab_attributes
-                                                .fetch("runtime_dependencies", []).then { |deps| deps || [] }
-                                                .each_with_object({}) { |dep, h| h[dep["full_name"]] = dep }
-                                                .freeze
+      bottle_tab_attributes = formula.bottle_tab_attributes
+      @bottle_tab_runtime_dependencies = bottle_tab_attributes
+                                         .fetch("runtime_dependencies", []).then { |deps| deps || [] }
+                                         .each_with_object({}) { |dep, h| h[dep["full_name"]] = dep }
+                                         .freeze
+
+      if (bottle_tag = formula.bottle_for_tag(Utils::Bottles.tag)&.tag) &&
+         bottle_tag.system != :all
+        # Extract the OS version the bottle was built on.
+        # This ensures that when installing older bottles (e.g. Sonoma bottle on Sequoia),
+        # we resolve dependencies according to the bottle's built OS, not the current OS.
+        @bottle_built_os_version = bottle_tab_attributes.dig("built_on", "os_version")
+      end
     rescue Resource::BottleManifest::Error
       # If we can't get the bottle manifest, assume a full dependencies install.
     end
@@ -772,14 +783,14 @@ def expand_dependencies_for_formula(formula, inherited_options)
       keep_build_test ||= dep.build? && !install_bottle_for?(dependent, build) &&
                           (formula.head? || !dependent.latest_version_installed?)
 
-      bottle_runtime_version = @bottle_tab_runtime_dependencies.dig(dep.name, "version").presence
-      bottle_runtime_version = Version.new(bottle_runtime_version) if bottle_runtime_version
-      bottle_runtime_revision = @bottle_tab_runtime_dependencies.dig(dep.name, "revision")
+      minimum_version = @bottle_tab_runtime_dependencies.dig(dep.name, "version").presence
+      minimum_version = Version.new(minimum_version) if minimum_version
+      minimum_revision = @bottle_tab_runtime_dependencies.dig(dep.name, "revision")
+      bottle_os_version = @bottle_built_os_version
 
       if dep.prune_from_option?(build) || ((dep.build? || dep.test?) && !keep_build_test)
         Dependency.prune
-      elsif dep.satisfied?(inherited_options[dep.name], minimum_version:  bottle_runtime_version,
-                                                        minimum_revision: bottle_runtime_revision)
+      elsif dep.satisfied?(inherited_options[dep.name], minimum_version:, minimum_revision:, bottle_os_version:)
         Dependency.skip
       end
     end
diff --git a/Library/Homebrew/test/dependency_spec.rb b/Library/Homebrew/test/dependency_spec.rb
index 2fbb9cea55075..846ba1fd59ed5 100644
--- a/Library/Homebrew/test/dependency_spec.rb
+++ b/Library/Homebrew/test/dependency_spec.rb
@@ -122,4 +122,40 @@
       expect(dep).not_to be_test
     end
   end
+
+  describe "Dependency#installed? with bottle_os_version" do
+    subject(:dependency) { described_class.new("foo") }
+
+    it "accepts macOS bottle_os_version parameter" do
+      expect { dependency.installed?(bottle_os_version: "macOS 14") }.not_to raise_error
+    end
+
+    it "accepts Ubuntu bottle_os_version parameter" do
+      expect { dependency.installed?(bottle_os_version: "Ubuntu 22.04") }.not_to raise_error
+    end
+  end
+
+  describe "Dependency#satisfied? with bottle_os_version" do
+    subject(:dependency) { described_class.new("foo") }
+
+    it "accepts bottle_os_version parameter" do
+      expect { dependency.satisfied?([], bottle_os_version: "macOS 14") }.not_to raise_error
+    end
+
+    it "accepts Ubuntu bottle_os_version parameter" do
+      expect { dependency.installed?(bottle_os_version: "Ubuntu 22.04") }.not_to raise_error
+    end
+  end
+
+  describe "UsesFromMacOSDependency#installed? with bottle_os_version" do
+    subject(:uses_from_macos) { described_class.new("foo", bounds: { since: :sonoma }) }
+
+    it "accepts macOS bottle_os_version parameter" do
+      expect { uses_from_macos.installed?(bottle_os_version: "macOS 14") }.not_to raise_error
+    end
+
+    it "accepts Ubuntu bottle_os_version parameter" do
+      expect { uses_from_macos.installed?(bottle_os_version: "Ubuntu 22.04") }.not_to raise_error
+    end
+  end
 end