diff --git a/Library/Homebrew/build.rb b/Library/Homebrew/build.rb
index b432fdca82..5ee369389a 100644
--- a/Library/Homebrew/build.rb
+++ b/Library/Homebrew/build.rb
@@ -127,9 +127,10 @@ class Build
       formula.update_head_version
 
       formula.brew(
-        fetch:       false,
-        keep_tmp:    args.keep_tmp?,
-        interactive: args.interactive?,
+        fetch:         false,
+        keep_tmp:      args.keep_tmp?,
+        debug_symbols: args.debug_symbols?,
+        interactive:   args.interactive?,
       ) do
         with_env(
           # For head builds, HOMEBREW_FORMULA_PREFIX should include the commit,
diff --git a/Library/Homebrew/cli/args.rbi b/Library/Homebrew/cli/args.rbi
index 32b1cd8e6e..af6802f6ac 100644
--- a/Library/Homebrew/cli/args.rbi
+++ b/Library/Homebrew/cli/args.rbi
@@ -87,6 +87,9 @@ module Homebrew
       sig { returns(T::Boolean) }
       def keep_tmp?; end
 
+      sig { returns(T::Boolean) }
+      def debug_symbols?; end
+
       sig { returns(T::Boolean) }
       def overwrite?; end
 
diff --git a/Library/Homebrew/cmd/install.rb b/Library/Homebrew/cmd/install.rb
index cff794979e..6848e982b5 100644
--- a/Library/Homebrew/cmd/install.rb
+++ b/Library/Homebrew/cmd/install.rb
@@ -91,6 +91,11 @@ module Homebrew
         [:switch, "--keep-tmp", {
           description: "Retain the temporary files created during installation.",
         }],
+        [:switch, "--debug-symbols", {
+          depends_on:  "--build-from-source",
+          description: "Generates debugging symbols during build. Source will be in temporary directory " \
+                       "which is retained. (see --keep-tmp)",
+        }],
         [:switch, "--build-bottle", {
           description: "Prepare the formula for eventual bottling during installation, skipping any " \
                        "post-install steps.",
@@ -232,6 +237,7 @@ module Homebrew
       git:                        args.git?,
       interactive:                args.interactive?,
       keep_tmp:                   args.keep_tmp?,
+      debug_symbols:              args.debug_symbols?,
       force:                      args.force?,
       overwrite:                  args.overwrite?,
       debug:                      args.debug?,
@@ -247,6 +253,7 @@ module Homebrew
       build_from_source_formulae: args.build_from_source_formulae,
       interactive:                args.interactive?,
       keep_tmp:                   args.keep_tmp?,
+      debug_symbols:              args.debug_symbols?,
       force:                      args.force?,
       debug:                      args.debug?,
       quiet:                      args.quiet?,
diff --git a/Library/Homebrew/cmd/reinstall.rb b/Library/Homebrew/cmd/reinstall.rb
index bc6bca5053..bb8b4844cc 100644
--- a/Library/Homebrew/cmd/reinstall.rb
+++ b/Library/Homebrew/cmd/reinstall.rb
@@ -57,6 +57,11 @@ module Homebrew
         [:switch, "--keep-tmp", {
           description: "Retain the temporary files created during installation.",
         }],
+        [:switch, "--debug-symbols", {
+          depends_on:  "--build-from-source",
+          description: "Generates debugging symbols during build. Source will be in temporary directory " \
+                       "which is retained. (see --keep-tmp)",
+        }],
         [:switch, "--display-times", {
           env:         :display_install_times,
           description: "Print install times for each formula at the end of the run.",
@@ -115,6 +120,7 @@ module Homebrew
         build_from_source_formulae: args.build_from_source_formulae,
         interactive:                args.interactive?,
         keep_tmp:                   args.keep_tmp?,
+        debug_symbols:              args.debug_symbols?,
         force:                      args.force?,
         debug:                      args.debug?,
         quiet:                      args.quiet?,
@@ -132,6 +138,7 @@ module Homebrew
       build_from_source_formulae: args.build_from_source_formulae,
       interactive:                args.interactive?,
       keep_tmp:                   args.keep_tmp?,
+      debug_symbols:              args.debug_symbols?,
       force:                      args.force?,
       debug:                      args.debug?,
       quiet:                      args.quiet?,
diff --git a/Library/Homebrew/cmd/upgrade.rb b/Library/Homebrew/cmd/upgrade.rb
index ec7520a7c3..3496c7274b 100644
--- a/Library/Homebrew/cmd/upgrade.rb
+++ b/Library/Homebrew/cmd/upgrade.rb
@@ -68,6 +68,11 @@ module Homebrew
         [:switch, "--keep-tmp", {
           description: "Retain the temporary files created during installation.",
         }],
+        [:switch, "--debug-symbols", {
+          depends_on:  "--build-from-source",
+          description: "Generates debugging symbols during build. Source will be in temporary directory " \
+                       "which is retained. (see --keep-tmp)",
+        }],
         [:switch, "--display-times", {
           env:         :display_install_times,
           description: "Print install times for each package at the end of the run.",
@@ -185,6 +190,7 @@ module Homebrew
       build_from_source_formulae: args.build_from_source_formulae,
       interactive:                args.interactive?,
       keep_tmp:                   args.keep_tmp?,
+      debug_symbols:              args.debug_symbols?,
       force:                      args.force?,
       debug:                      args.debug?,
       quiet:                      args.quiet?,
@@ -200,6 +206,7 @@ module Homebrew
       build_from_source_formulae: args.build_from_source_formulae,
       interactive:                args.interactive?,
       keep_tmp:                   args.keep_tmp?,
+      debug_symbols:              args.debug_symbols?,
       force:                      args.force?,
       debug:                      args.debug?,
       quiet:                      args.quiet?,
diff --git a/Library/Homebrew/extend/ENV/shared.rb b/Library/Homebrew/extend/ENV/shared.rb
index 381ceccfdb..bccd15aaf5 100644
--- a/Library/Homebrew/extend/ENV/shared.rb
+++ b/Library/Homebrew/extend/ENV/shared.rb
@@ -315,6 +315,9 @@ module SharedEnvExtension
   sig { void }
   def permit_arch_flags; end
 
+  sig { void }
+  def debug_symbols; end
+
   # @private
   sig { params(cc: T.any(Symbol, String)).returns(T::Boolean) }
   def compiler_any_clang?(cc = compiler)
diff --git a/Library/Homebrew/extend/os/mac/keg.rb b/Library/Homebrew/extend/os/mac/keg.rb
index a6c03b82d7..a1fde91b14 100644
--- a/Library/Homebrew/extend/os/mac/keg.rb
+++ b/Library/Homebrew/extend/os/mac/keg.rb
@@ -67,7 +67,7 @@ class Keg
     binary_executable_or_library_files.each do |file|
       odebug "Extracting symbols #{file}"
 
-      result = system_command("dsymutil", args: [file])
+      result = system_command("dsymutil", args: [file], print_stderr: false)
       next if result.success?
 
       # If it fails again, error out
diff --git a/Library/Homebrew/formula.rb b/Library/Homebrew/formula.rb
index 17488e0ed1..87084de97d 100644
--- a/Library/Homebrew/formula.rb
+++ b/Library/Homebrew/formula.rb
@@ -1273,11 +1273,11 @@ class Formula
   # Yields |self,staging| with current working directory set to the uncompressed tarball
   # where staging is a {Mktemp} staging context.
   # @private
-  def brew(fetch: true, keep_tmp: false, interactive: false)
+  def brew(fetch: true, keep_tmp: false, debug_symbols: false, interactive: false)
     @prefix_returns_versioned_prefix = true
     active_spec.fetch if fetch
     stage(interactive: interactive) do |staging|
-      staging.retain! if keep_tmp
+      staging.retain! if keep_tmp || debug_symbols
 
       prepare_patches
       fetch_patches if fetch
diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index 611ec46643..52e1e9881c 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -59,6 +59,7 @@ class FormulaInstaller
     git: false,
     interactive: false,
     keep_tmp: false,
+    debug_symbols: false,
     cc: nil,
     options: Options.new,
     force: false,
@@ -72,8 +73,7 @@ class FormulaInstaller
     @force = force
     @overwrite = overwrite
     @keep_tmp = keep_tmp
-    # Just for this proof of concept
-    @debug_symbols = keep_tmp
+    @debug_symbols = debug_symbols
     @link_keg = !formula.keg_only? || link_keg
     @show_header = show_header
     @ignore_deps = ignore_deps
@@ -691,6 +691,7 @@ class FormulaInstaller
       include_test_formulae:      @include_test_formulae,
       build_from_source_formulae: @build_from_source_formulae,
       keep_tmp:                   keep_tmp?,
+      debug_symbols:              debug_symbols?,
       force:                      force?,
       debug:                      debug?,
       quiet:                      quiet?,
@@ -744,6 +745,7 @@ class FormulaInstaller
         include_test_formulae:      @include_test_formulae,
         build_from_source_formulae: @build_from_source_formulae,
         keep_tmp:                   keep_tmp?,
+        debug_symbols:              debug_symbols?,
         force:                      force?,
         debug:                      debug?,
         quiet:                      quiet?,
@@ -877,6 +879,9 @@ class FormulaInstaller
     args << "--debug" if debug?
     args << "--cc=#{@cc}" if @cc
     args << "--keep-tmp" if keep_tmp?
+    args << "--debug-symbols" if debug_symbols?
+    # Avoids dependecy error on flag
+    args << "--build-from-source" if build_from_source? && debug_symbols?
 
     if @env.present?
       args << "--env=#{@env}"
diff --git a/Library/Homebrew/install.rb b/Library/Homebrew/install.rb
index 9ab565d431..3d838dac3e 100644
--- a/Library/Homebrew/install.rb
+++ b/Library/Homebrew/install.rb
@@ -269,6 +269,7 @@ module Homebrew
       git: false,
       interactive: false,
       keep_tmp: false,
+      debug_symbols: false,
       force: false,
       overwrite: false,
       debug: false,
@@ -293,6 +294,7 @@ module Homebrew
           git:                        git,
           interactive:                interactive,
           keep_tmp:                   keep_tmp,
+          debug_symbols:              debug_symbols,
           force:                      force,
           overwrite:                  overwrite,
           debug:                      debug,
diff --git a/Library/Homebrew/reinstall.rb b/Library/Homebrew/reinstall.rb
index 2c9c0ee430..f260d041b7 100644
--- a/Library/Homebrew/reinstall.rb
+++ b/Library/Homebrew/reinstall.rb
@@ -16,6 +16,7 @@ module Homebrew
     build_from_source_formulae: [],
     interactive: false,
     keep_tmp: false,
+    debug_symbols: false,
     force: false,
     debug: false,
     quiet: false,
@@ -48,6 +49,7 @@ module Homebrew
         git:                        git,
         interactive:                interactive,
         keep_tmp:                   keep_tmp,
+        debug_symbols:              debug_symbols,
         force:                      force,
         debug:                      debug,
         quiet:                      quiet,
diff --git a/Library/Homebrew/upgrade.rb b/Library/Homebrew/upgrade.rb
index c9f0acc576..54e3223c18 100644
--- a/Library/Homebrew/upgrade.rb
+++ b/Library/Homebrew/upgrade.rb
@@ -24,6 +24,7 @@ module Homebrew
       build_from_source_formulae: [],
       interactive: false,
       keep_tmp: false,
+      debug_symbols: false,
       force: false,
       debug: false,
       quiet: false,
@@ -61,6 +62,7 @@ module Homebrew
             build_from_source_formulae: build_from_source_formulae,
             interactive:                interactive,
             keep_tmp:                   keep_tmp,
+            debug_symbols:              debug_symbols,
             force:                      force,
             debug:                      debug,
             quiet:                      quiet,
@@ -128,6 +130,7 @@ module Homebrew
       build_from_source_formulae: [],
       interactive: false,
       keep_tmp: false,
+      debug_symbols: false,
       force: false,
       debug: false,
       quiet: false,
@@ -161,6 +164,7 @@ module Homebrew
           build_from_source_formulae: build_from_source_formulae,
           interactive:                interactive,
           keep_tmp:                   keep_tmp,
+          debug_symbols:              debug_symbols,
           force:                      force,
           debug:                      debug,
           quiet:                      quiet,
@@ -254,6 +258,7 @@ module Homebrew
       build_from_source_formulae: [],
       interactive: false,
       keep_tmp: false,
+      debug_symbols: false,
       force: false,
       debug: false,
       quiet: false,
@@ -339,6 +344,7 @@ module Homebrew
           build_from_source_formulae: build_from_source_formulae,
           interactive:                interactive,
           keep_tmp:                   keep_tmp,
+          debug_symbols:              debug_symbols,
           force:                      force,
           debug:                      debug,
           quiet:                      quiet,
@@ -407,6 +413,7 @@ module Homebrew
           build_from_source_formulae: build_from_source_formulae + [formula.full_name],
           interactive:                interactive,
           keep_tmp:                   keep_tmp,
+          debug_symbols:              debug_symbols,
           force:                      force,
           debug:                      debug,
           quiet:                      quiet,