diff --git a/src/cli/lib/deployment.test.ts b/src/cli/lib/deployment.test.ts
index 1d6bd97..656d829 100644
--- a/src/cli/lib/deployment.test.ts
+++ b/src/cli/lib/deployment.test.ts
@@ -52,17 +52,29 @@ test("env var changes", () => {
 });
 
 test("git ignore changes", () => {
+  // Handle additions
   expect(changesToGitIgnore(null)).toEqual(".env.local\n");
-
   expect(changesToGitIgnore("")).toEqual("\n.env.local\n");
-
   expect(changesToGitIgnore(".env")).toEqual(".env\n.env.local\n");
+  expect(changesToGitIgnore("# .env.local")).toEqual(
+    "# .env.local\n.env.local\n",
+  );
 
+  // Handle existing
   expect(changesToGitIgnore(".env.local")).toEqual(null);
   expect(changesToGitIgnore(".env.*")).toEqual(null);
   expect(changesToGitIgnore(".env*")).toEqual(null);
+  expect(changesToGitIgnore(".env*.local")).toEqual(null);
+  expect(changesToGitIgnore("*.local")).toEqual(null);
+  expect(changesToGitIgnore("# convex env\n.env.local")).toEqual(null);
+
+  // Handle Windows
+  expect(changesToGitIgnore(".env.local\r")).toEqual(null);
+
+  // Handle whitespace
+  expect(changesToGitIgnore(" .env.local ")).toEqual(null);
 
-  // This is wonky, but will guide the user to solve the problem
+  // Add .env.local (even if it's negated) to guide the user to solve the problem
   expect(changesToGitIgnore("!.env.local")).toEqual(
     "!.env.local\n.env.local\n",
   );
diff --git a/src/cli/lib/deployment.ts b/src/cli/lib/deployment.ts
index 56cd68d..a36b226 100644
--- a/src/cli/lib/deployment.ts
+++ b/src/cli/lib/deployment.ts
@@ -146,14 +146,23 @@ export function changesToGitIgnore(existingFile: string | null): string | null {
     return `${ENV_VAR_FILE_PATH}\n`;
   }
   const gitIgnoreLines = existingFile.split("\n");
-  const envVarFileIgnored = gitIgnoreLines.some(
-    (line) =>
-      line === ".env.local" ||
-      line === ".env.*" ||
-      line === ".env*" ||
-      line === "*.local" ||
-      line === ".env*.local",
-  );
+  const envVarFileIgnored = gitIgnoreLines.some((line) => {
+    // Remove extra whitespace
+    const trimmedLine = line.trim();
+
+    // Ignore negated patterns and comments
+    if (trimmedLine.startsWith("!") || trimmedLine.startsWith("#"))
+      return false;
+
+    const envIgnorePatterns = [
+      // .env.local, .env.*, .env*
+      /^\.env(\.local|\.\*|\*)$/,
+      // .env*.local, *.local
+      /^(\.env)?\*\.local$/,
+    ];
+
+    return envIgnorePatterns.some((pattern) => pattern.test(trimmedLine));
+  });
   if (!envVarFileIgnored) {
     return `${existingFile}\n${ENV_VAR_FILE_PATH}\n`;
   } else {