diff --git a/Library/Homebrew/dev-cmd/bump-cask-pr.rb b/Library/Homebrew/dev-cmd/bump-cask-pr.rb
index bf9d9aafe5..b132275ed9 100644
--- a/Library/Homebrew/dev-cmd/bump-cask-pr.rb
+++ b/Library/Homebrew/dev-cmd/bump-cask-pr.rb
@@ -71,7 +71,16 @@ module Homebrew
         # Use the user's browser, too.
         ENV["BROWSER"] = EnvConfig.browser
 
-        cask = args.named.to_casks.fetch(0)
+        @cask_retried = T.let(false, T.nilable(T::Boolean))
+        cask = begin
+          args.named.to_casks.fetch(0)
+        rescue Cask::CaskUnavailableError
+          raise if @cask_retried
+
+          CoreCaskTap.instance.install(force: true)
+          @cask_retried = true
+          retry
+        end
 
         odie "This cask is not in a tap!" if cask.tap.blank?
         odie "This cask's tap is not a Git repository!" unless cask.tap.git?
diff --git a/Library/Homebrew/dev-cmd/bump-formula-pr.rb b/Library/Homebrew/dev-cmd/bump-formula-pr.rb
index f6d9d83b5e..98af7df840 100644
--- a/Library/Homebrew/dev-cmd/bump-formula-pr.rb
+++ b/Library/Homebrew/dev-cmd/bump-formula-pr.rb
@@ -105,14 +105,28 @@ module Homebrew
         # Use the user's browser, too.
         ENV["BROWSER"] = Homebrew::EnvConfig.browser
 
-        formula = args.named.to_formulae.first
-        raise FormulaUnspecifiedError if formula.blank?
+        @tap_retried = T.let(false, T.nilable(T::Boolean))
+        begin
+          formula = args.named.to_formulae.first
+          raise FormulaUnspecifiedError if formula.blank?
 
-        odie "This formula is disabled!" if formula.disabled?
-        odie "This formula is deprecated and does not build!" if formula.deprecation_reason == :does_not_build
-        tap = formula.tap
-        odie "This formula is not in a tap!" if tap.blank?
-        odie "This formula's tap is not a Git repository!" unless tap.git?
+          raise ArgumentError, "This formula is disabled!" if formula.disabled?
+          if formula.deprecation_reason == :does_not_build
+            raise ArgumentError, "This formula is deprecated and does not build!"
+          end
+
+          tap = formula.tap
+          raise ArgumentError, "This formula is not in a tap!" if tap.blank?
+          raise ArgumentError, "This formula's tap is not a Git repository!" unless tap.git?
+
+          formula
+        rescue ArgumentError => e
+          odie e.message if @tap_retried
+
+          CoreTap.instance.install(force: true)
+          @tap_retried = true
+          retry
+        end
 
         odie <<~EOS unless tap.allow_bump?(formula.name)
           Whoops, the #{formula.name} formula has its version update