diff --git a/Library/Homebrew/extend/os/mac/diagnostic.rb b/Library/Homebrew/extend/os/mac/diagnostic.rb
index a2d6f19a72..c8439b06cd 100644
--- a/Library/Homebrew/extend/os/mac/diagnostic.rb
+++ b/Library/Homebrew/extend/os/mac/diagnostic.rb
@@ -433,9 +433,13 @@ module Homebrew
         locator = MacOS.sdk_locator
 
         source = if locator.source == :clt
+          return if MacOS::CLT.below_minimum_version? # Handled by other diagnostics.
+
           update_instructions = MacOS::CLT.update_instructions
           "Command Line Tools (CLT)"
         else
+          return if MacOS::Xcode.below_minimum_version? # Handled by other diagnostics.
+
           update_instructions = MacOS::Xcode.update_instructions
           "Xcode"
         end
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/expat.pc b/Library/Homebrew/os/mac/pkgconfig/11/expat.pc
index 5559111ea9..43370a8aca 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/expat.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/expat.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/libcurl.pc b/Library/Homebrew/os/mac/pkgconfig/11/libcurl.pc
index ae14a734c8..b1fe8501fb 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/libcurl.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/libcurl.pc
@@ -23,7 +23,7 @@
 # This should most probably benefit from getting a "Requires:" field added
 # dynamically by configure.
 #
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/libedit.pc b/Library/Homebrew/os/mac/pkgconfig/11/libedit.pc
index e56b183c31..72fa1e609b 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/libedit.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/libedit.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/libexslt.pc b/Library/Homebrew/os/mac/pkgconfig/11/libexslt.pc
index a06775b570..f3cdef0613 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/libexslt.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/libexslt.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/libffi.pc b/Library/Homebrew/os/mac/pkgconfig/11/libffi.pc
index 21d6e56837..644b372932 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/libffi.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/libffi.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/libxml-2.0.pc b/Library/Homebrew/os/mac/pkgconfig/11/libxml-2.0.pc
index fa6272983e..d7cb87c472 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/libxml-2.0.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/libxml-2.0.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/libxslt.pc b/Library/Homebrew/os/mac/pkgconfig/11/libxslt.pc
index 28a3326b88..6d88788062 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/libxslt.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/libxslt.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/ncurses.pc b/Library/Homebrew/os/mac/pkgconfig/11/ncurses.pc
index b8d37fcdea..ce7159092b 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/ncurses.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/ncurses.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/ncursesw.pc b/Library/Homebrew/os/mac/pkgconfig/11/ncursesw.pc
index 001cb7298b..4db4c043f4 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/ncursesw.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/ncursesw.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/sqlite3.pc b/Library/Homebrew/os/mac/pkgconfig/11/sqlite3.pc
index 626863163d..f6a4dadaaa 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/sqlite3.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/sqlite3.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/uuid.pc b/Library/Homebrew/os/mac/pkgconfig/11/uuid.pc
index b77f88b475..e679e71039 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/uuid.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/uuid.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/pkgconfig/11/zlib.pc b/Library/Homebrew/os/mac/pkgconfig/11/zlib.pc
index e9b2cc6698..6193752e3f 100644
--- a/Library/Homebrew/os/mac/pkgconfig/11/zlib.pc
+++ b/Library/Homebrew/os/mac/pkgconfig/11/zlib.pc
@@ -1,4 +1,4 @@
-homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk
+homebrew_sdkroot=/Library/Developer/CommandLineTools/SDKs/MacOSX11.sdk
 prefix=${homebrew_sdkroot}/usr
 exec_prefix=/usr
 libdir=${exec_prefix}/lib
diff --git a/Library/Homebrew/os/mac/sdk.rb b/Library/Homebrew/os/mac/sdk.rb
index 164c095b09..13ee10fc70 100644
--- a/Library/Homebrew/os/mac/sdk.rb
+++ b/Library/Homebrew/os/mac/sdk.rb
@@ -9,7 +9,8 @@ module OS
     #
     # @api private
     class SDK
-      VERSIONED_SDK_REGEX = /MacOSX(\d+\.\d+)\.sdk$/.freeze
+      # 11.x SDKs are explicitly excluded - we want the MacOSX11.sdk symlink instead.
+      VERSIONED_SDK_REGEX = /MacOSX(10\.\d+|\d+)\.sdk$/.freeze
 
       attr_reader :version, :path, :source
 
@@ -41,24 +42,23 @@ module OS
         # Bail out if there is no SDK prefix at all
         return @all_sdks unless File.directory? sdk_prefix
 
-        # Use unversioned SDK path on Big Sur to avoid issues such as:
-        # https://github.com/Homebrew/homebrew-core/issues/67075
-        unversioned_sdk_path = Pathname.new("#{sdk_prefix}/MacOSX.sdk")
-        version = read_sdk_version(unversioned_sdk_path)
-        if version && version >= :big_sur
-          unversioned_sdk_version = version
-          @all_sdks << SDK.new(unversioned_sdk_version, unversioned_sdk_path, source)
-        end
-
         Dir["#{sdk_prefix}/MacOSX*.sdk"].each do |sdk_path|
           next unless sdk_path.match?(SDK::VERSIONED_SDK_REGEX)
 
           version = read_sdk_version(Pathname.new(sdk_path))
-          next if version.nil? || version == unversioned_sdk_version
+          next if version.nil?
 
           @all_sdks << SDK.new(version, sdk_path, source)
         end
 
+        # Fall back onto unversioned SDK if we've not found a suitable SDK
+        if @all_sdks.empty?
+          sdk_path = Pathname.new("#{sdk_prefix}/MacOSX.sdk")
+          if (version = read_sdk_version(sdk_path))
+            @all_sdks << SDK.new(version, sdk_path, source)
+          end
+        end
+
         @all_sdks
       end
 
diff --git a/Library/Homebrew/os/mac/xcode.rb b/Library/Homebrew/os/mac/xcode.rb
index 17f916fe20..80353f2453 100755
--- a/Library/Homebrew/os/mac/xcode.rb
+++ b/Library/Homebrew/os/mac/xcode.rb
@@ -336,7 +336,7 @@ module OS
       def minimum_version
         case MacOS.version
         when "12" then "13.0.0"
-        when "11" then "12.0.0"
+        when "11" then "12.5.0"
         when "10.15" then "11.0.0"
         when "10.14" then "10.0.0"
         when "10.13" then "9.0.0"
diff --git a/Library/Homebrew/test/os/mac/diagnostic_spec.rb b/Library/Homebrew/test/os/mac/diagnostic_spec.rb
index e7bd09de12..c0a0e2573e 100644
--- a/Library/Homebrew/test/os/mac/diagnostic_spec.rb
+++ b/Library/Homebrew/test/os/mac/diagnostic_spec.rb
@@ -47,6 +47,8 @@ describe Homebrew::Diagnostic::Checks do
     before do
       allow(DevelopmentTools).to receive(:installed?).and_return(true)
       allow(OS::Mac).to receive(:version).and_return(macos_version)
+      allow(OS::Mac::CLT).to receive(:below_minimum_version?).and_return(false)
+      allow(OS::Mac::Xcode).to receive(:below_minimum_version?).and_return(false)
     end
 
     it "doesn't trigger when SDK root is not needed" do