diff --git a/packages/safe-chain/src/shell-integration/supported-shells/bash.spec.js b/packages/safe-chain/src/shell-integration/supported-shells/bash.spec.js
index e23addb..ebe0676 100644
--- a/packages/safe-chain/src/shell-integration/supported-shells/bash.spec.js
+++ b/packages/safe-chain/src/shell-integration/supported-shells/bash.spec.js
@@ -8,6 +8,8 @@ import { knownAikidoTools } from "../helpers.js";
 describe("Bash shell integration", () => {
   let mockStartupFile;
   let bash;
+  let windowsCygwinPath = "";
+  let platform = "linux";
 
   beforeEach(async () => {
     // Create temporary startup file for testing
@@ -37,6 +39,35 @@ describe("Bash shell integration", () => {
     mock.module("child_process", {
       namedExports: {
         execSync: () => mockStartupFile,
+        spawnSync: (command, args) => {
+          if (platform !== "win32") {
+            return { status: 0 };
+          }
+
+          if (command === "where" && args[0] === "cygpath") {
+            return {
+              status: 0,
+              stdout: Buffer.from("C:\\cygwin64\\bin\\cygpath.exe\n"),
+            };
+          }
+
+          if (
+            command === "cygpath" &&
+            args[0] === "-w" &&
+            args[1] === mockStartupFile
+          ) {
+            return {
+              status: 0,
+              stdout: windowsCygwinPath + "\n",
+            };
+          }
+        },
+      },
+    });
+
+    mock.module("os", {
+      namedExports: {
+        platform: () => platform,
       },
     });
 
@@ -52,6 +83,7 @@ describe("Bash shell integration", () => {
 
     // Reset mocks
     mock.reset();
+    platform = "linux";
   });
 
   describe("isInstalled", () => {
@@ -77,6 +109,23 @@ describe("Bash shell integration", () => {
         )
       );
     });
+
+    it("should use the correct startup file for cygwin bash on Windows", () => {
+      platform = "win32";
+      // set windows path to the correct filename
+      windowsCygwinPath = mockStartupFile;
+      mockStartupFile = "DUMMY"; // This will be overridden by the mocked execSync
+
+      const result = bash.setup();
+      assert.strictEqual(result, true);
+
+      const content = fs.readFileSync(windowsCygwinPath, "utf-8");
+      assert.ok(
+        content.includes(
+          "source ~/.safe-chain/scripts/init-posix.sh # Safe-chain bash initialization script"
+        )
+      );
+    });
   });
 
   describe("teardown", () => {