diff --git a/.github/workflows/ci.generate.ts b/.github/workflows/ci.generate.ts
index 2d8dbf2509a384..f5649b69bc14ca 100755
--- a/.github/workflows/ci.generate.ts
+++ b/.github/workflows/ci.generate.ts
@@ -299,9 +299,16 @@ function withCondition(
   step: Record<string, unknown>,
   condition: string,
 ): Record<string, unknown> {
+  function maybeParens(condition: string) {
+    if (condition.includes("&&") || condition.includes("||")) {
+      return `(${condition})`;
+    } else {
+      return condition;
+    }
+  }
   return {
     ...step,
-    if: "if" in step ? `${condition} && (${step.if})` : condition,
+    if: "if" in step ? `${maybeParens(condition)} && (${step.if})` : condition,
   };
 }
 
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 13ca1b15f7a34d..2c7df65b32b2be 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -189,7 +189,7 @@ jobs:
           python-version: 3.11
         if: '!(matrix.skip) && (matrix.os != ''linux'' || matrix.arch != ''aarch64'')'
       - name: Remove unused versions of Python
-        if: '!(matrix.skip) && (matrix.os != ''linux'' || matrix.arch != ''aarch64'' && (matrix.os == ''windows''))'
+        if: '!(matrix.skip) && ((matrix.os != ''linux'' || matrix.arch != ''aarch64'') && (matrix.os == ''windows''))'
         shell: pwsh
         run: |-
           $env:PATH -split ";" |