diff --git a/Library/Homebrew/os/mac/version.rb b/Library/Homebrew/os/mac/version.rb
index 321116c7b2..4eda2de6ed 100644
--- a/Library/Homebrew/os/mac/version.rb
+++ b/Library/Homebrew/os/mac/version.rb
@@ -13,6 +13,8 @@ module OS
     class Version < ::Version
       extend T::Sig
 
+      # TODO: when removing symbols here, ensure that they are added to
+      # DEPRECATED_MACOS_VERSIONS in MacOSRequirement.
       SYMBOLS = {
         monterey:    "12",
         big_sur:     "11",
@@ -21,22 +23,21 @@ module OS
         high_sierra: "10.13",
         sierra:      "10.12",
         el_capitan:  "10.11",
-        # TODO: remove after 3.5.0 has been shipped and this is implicitly
-        # odisabled and we've cleaned up all tap references.
-        yosemite:    "10.10",
       }.freeze
 
       # TODO: bump version when new macOS is released or announced
       # and also update references in docs/Installation.md and
       # https://github.com/Homebrew/install/blob/HEAD/install.sh
-      MACOS_NEWEST_UNSUPPORTED = "13"
-      private_constant :MACOS_NEWEST_UNSUPPORTED
+      NEWEST_UNSUPPORTED = "13"
+      private_constant :NEWEST_UNSUPPORTED
 
       # TODO: bump version when new macOS is released and also update
       # references in docs/Installation.md and
       # https://github.com/Homebrew/install/blob/HEAD/install.sh
-      MACOS_OLDEST_SUPPORTED = "10.15"
-      private_constant :MACOS_OLDEST_SUPPORTED
+      OLDEST_SUPPORTED = "10.15"
+      private_constant :OLDEST_SUPPORTED
+
+      OLDEST_ALLOWED = "10.11"
 
       sig { params(version: Symbol).returns(T.attached_class) }
       def self.from_symbol(version)
@@ -89,12 +90,12 @@ module OS
 
       sig { returns(T::Boolean) }
       def outdated_release?
-        self < MACOS_OLDEST_SUPPORTED
+        self < OLDEST_SUPPORTED
       end
 
       sig { returns(T::Boolean) }
       def prerelease?
-        self >= MACOS_NEWEST_UNSUPPORTED
+        self >= NEWEST_UNSUPPORTED
       end
 
       # For {OS::Mac::Version} compatibility.
diff --git a/Library/Homebrew/requirements/macos_requirement.rb b/Library/Homebrew/requirements/macos_requirement.rb
index 5284acb114..f900a626d0 100644
--- a/Library/Homebrew/requirements/macos_requirement.rb
+++ b/Library/Homebrew/requirements/macos_requirement.rb
@@ -13,15 +13,41 @@ class MacOSRequirement < Requirement
 
   attr_reader :comparator, :version
 
+  # TODO: when Yosemite is removed here, keep these around as empty arrays so we
+  # can keep the deprecation/disabling code the same.
+  DISABLED_MACOS_VERSIONS = [].freeze
+  DEPRECATED_MACOS_VERSIONS = [
+    :yosemite,
+  ].freeze
+
   def initialize(tags = [], comparator: ">=")
-    @version = if comparator == "==" && tags.first.respond_to?(:map)
-      tags.shift.map { |s| MacOS::Version.from_symbol(s) }
-    else
-      MacOS::Version.from_symbol(tags.shift) unless tags.empty?
+    @version = begin
+      if comparator == "==" && tags.first.respond_to?(:map)
+        tags.first.map { |s| MacOS::Version.from_symbol(s) }
+      else
+        MacOS::Version.from_symbol(tags.first) unless tags.empty?
+      end
+    rescue MacOSVersionError => e
+      if DISABLED_MACOS_VERSIONS.include?(e.version)
+        odisabled "depends_on :macos => :#{e.version}"
+      elsif DEPRECATED_MACOS_VERSIONS.include?(e.version)
+        odeprecated "depends_on :macos => :#{e.version}"
+      else
+        raise
+      end
+
+      # Array of versions: remove the bad ones and try again.
+      if tags.first.respond_to?(:reject)
+        tags = [tags.first.reject { |s| s == e.version }, tags[1..]]
+        retry
+      end
+
+      # Otherwise fallback to the oldest allowed if comparator is >=.
+      MacOS::Version.new(MacOS::Version::OLDEST_ALLOWED) if comparator == ">="
     end
 
     @comparator = comparator
-    super(tags)
+    super(tags.drop(1))
   end
 
   def version_specified?