diff --git a/CHANGES b/CHANGES
index cd6079b847..32b08ba950 100644
--- a/CHANGES
+++ b/CHANGES
@@ -1,3 +1,7 @@
+7.2.0-dev.285 | 2025-03-10 08:28:54 -0700
+
+  * CI: Unconditionally upgrade pip on macOS (Tim Wojtulewicz, Corelight)
+
 7.2.0-dev.283 | 2025-03-10 06:11:40 -0700
 
   * Fix return types in docs for double_to_count and double_to_int (Tim Wojtulewicz, Corelight)
diff --git a/VERSION b/VERSION
index 62690f8385..cfc46c6f07 100644
--- a/VERSION
+++ b/VERSION
@@ -1 +1 @@
-7.2.0-dev.283
+7.2.0-dev.285
diff --git a/ci/macos/prepare.sh b/ci/macos/prepare.sh
index 19272e3de0..25ad859b33 100755
--- a/ci/macos/prepare.sh
+++ b/ci/macos/prepare.sh
@@ -9,8 +9,6 @@ brew update
 brew upgrade cmake
 brew install cppzmq openssl@3 swig bison flex ccache libmaxminddb dnsmasq
 
-if [ $(sw_vers -productVersion | cut -d '.' -f 1) -lt 14 ]; then
-    python3 -m pip install --upgrade pip
-fi
-
+# Upgrade pip so we have the --break-system-packages option.
+python3 -m pip install --upgrade pip
 python3 -m pip install --user --break-system-packages websockets