diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index 53b72b9428..8ea009c007 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -823,6 +823,7 @@ class FormulaInstaller
     if formula.name == "curl" &&
        !DevelopmentTools.curl_handles_most_https_certificates?
       ENV["HOMEBREW_CURL"] = formula.opt_bin/"curl"
+      Utils::Curl.clear_path_cache
     end
 
     caveats
diff --git a/Library/Homebrew/test/spec_helper.rb b/Library/Homebrew/test/spec_helper.rb
index d073166ac4..254af085a9 100644
--- a/Library/Homebrew/test/spec_helper.rb
+++ b/Library/Homebrew/test/spec_helper.rb
@@ -203,6 +203,7 @@ RSpec.configure do |config|
     FormulaInstaller.clear_attempted
     FormulaInstaller.clear_installed
     FormulaInstaller.clear_fetched
+    Utils::Curl.clear_path_cache
 
     TEST_DIRECTORIES.each(&:mkpath)
 
diff --git a/Library/Homebrew/utils/curl.rb b/Library/Homebrew/utils/curl.rb
index 5b094f7f07..0abfd0abb6 100644
--- a/Library/Homebrew/utils/curl.rb
+++ b/Library/Homebrew/utils/curl.rb
@@ -42,6 +42,10 @@ module Utils
       @curl_path ||= Utils.popen_read(curl_executable, "--homebrew=print-path").chomp.presence
     end
 
+    def clear_path_cache
+      @curl_path = nil
+    end
+
     sig {
       params(
         extra_args:      T.untyped,