diff --git a/Library/Homebrew/global.rb b/Library/Homebrew/global.rb
index 70506170f8..3597cfe82f 100644
--- a/Library/Homebrew/global.rb
+++ b/Library/Homebrew/global.rb
@@ -47,8 +47,10 @@ HOMEBREW_USER_AGENT_CURL = ENV.fetch("HOMEBREW_USER_AGENT_CURL").freeze
 HOMEBREW_USER_AGENT_RUBY =
   "#{ENV.fetch("HOMEBREW_USER_AGENT")} ruby/#{RUBY_VERSION}-p#{RUBY_PATCHLEVEL}"
 HOMEBREW_USER_AGENT_FAKE_SAFARI =
-  "Mozilla/5.0 (Macintosh; Intel Mac OS X 13_5_1) AppleWebKit/605.1.15 " \
-  "(KHTML, like Gecko) Version/16.5 Safari/605.1.15"
+  # Don't update this beyond 10.15.7 until Safari actually updates their
+  # user agent to be beyond 10.15.7 (not the case as-of macOS 14)
+  "Mozilla/5.0 (Macintosh; Intel Mac OS X 10_15_7) AppleWebKit/605.1.15 " \
+  "(KHTML, like Gecko) Version/17.0 Safari/605.1.15"
 HOMEBREW_GITHUB_PACKAGES_AUTH = ENV.fetch("HOMEBREW_GITHUB_PACKAGES_AUTH").freeze
 
 HOMEBREW_DEFAULT_PREFIX = ENV.fetch("HOMEBREW_GENERIC_DEFAULT_PREFIX").freeze
diff --git a/Library/Homebrew/test/download_strategies/curl_spec.rb b/Library/Homebrew/test/download_strategies/curl_spec.rb
index 2fe3dab6ad..ff94c94f7e 100644
--- a/Library/Homebrew/test/download_strategies/curl_spec.rb
+++ b/Library/Homebrew/test/download_strategies/curl_spec.rb
@@ -75,7 +75,7 @@ describe CurlDownloadStrategy do
             /curl/,
             hash_including(args: array_including_cons(
               "--user-agent",
-              a_string_matching(/Mozilla.*Mac OS X 13.*AppleWebKit/),
+              a_string_matching(/Mozilla.*Mac OS X 10_15_7.*AppleWebKit/),
             )),
           )
           .at_least(:once)