diff --git a/Library/Homebrew/test/utils/github_spec.rb b/Library/Homebrew/test/utils/github_spec.rb
index a132894f92..320704e196 100644
--- a/Library/Homebrew/test/utils/github_spec.rb
+++ b/Library/Homebrew/test/utils/github_spec.rb
@@ -31,9 +31,12 @@ describe GitHub do
 
   describe "::search_issues", :needs_network do
     it "queries GitHub issues with the passed parameters" do
-      results = subject.search_issues("brew search", repo: "Homebrew/brew", author: "avetamine", is: "closed")
+      results = subject.search_issues("brew search",
+                                      repo: "Homebrew/legacy-homebrew",
+                                      author: "MikeMcQuaid",
+                                      is: "closed")
       expect(results).not_to be_empty
-      expect(results.last["title"]).to eq("brew search : 422 Unprocessable Entity")
+      expect(results.first["title"]).to eq("Shall we run `brew update` automatically?")
     end
   end
 end
diff --git a/Library/Homebrew/utils/github.rb b/Library/Homebrew/utils/github.rb
index cbfe76a218..ba2abe7543 100644
--- a/Library/Homebrew/utils/github.rb
+++ b/Library/Homebrew/utils/github.rb
@@ -45,7 +45,7 @@ module GitHub
   class AuthenticationFailedError < Error
     def initialize(github_message)
       @github_message = github_message
-      message = "GitHub #{github_message}\n"
+      message = "GitHub #{github_message}:"
       if ENV["HOMEBREW_GITHUB_API_TOKEN"]
         message << <<~EOS
           HOMEBREW_GITHUB_API_TOKEN may be invalid or expired; check:
@@ -65,6 +65,18 @@ module GitHub
     end
   end
 
+  class ValidationFailedError < Error
+    def initialize(github_message, errors)
+      @github_message = if errors.empty?
+        github_message
+      else
+        "#{github_message}: #{errors}"
+      end
+
+      super(@github_message)
+    end
+  end
+
   def api_credentials
     @api_credentials ||= begin
       if ENV["HOMEBREW_GITHUB_API_TOKEN"]
@@ -231,6 +243,9 @@ module GitHub
       raise AuthenticationFailedError, message
     when "404"
       raise HTTPNotFoundError, message
+    when "422"
+      errors = json&.[]("errors") || []
+      raise ValidationFailedError.new(message, errors)
     else
       raise Error, message
     end