diff --git a/packages/backend/src/build-disk-image.ts b/packages/backend/src/build-disk-image.ts
index ab0f9f74..33648bef 100644
--- a/packages/backend/src/build-disk-image.ts
+++ b/packages/backend/src/build-disk-image.ts
@@ -31,17 +31,12 @@ const telemetryLogger = extensionApi.env.createTelemetryLogger();
 export async function buildDiskImage(imageData: unknown, history: History) {
   // Before we do ANYTHING, we should be checking to see if the podman machine is rootful or not
   // as that's a requirement for bootc-image-builder to work correctly.
-
-  // Only do this check on Windows or Mac
-
-  if (!machineUtils.isLinux()) {
-    const isRootful = await machineUtils.isPodmanMachineRootful();
-    if (!isRootful) {
-      await extensionApi.window.showErrorMessage(
-        'The podman machine is not set as rootful. Please recreate the podman machine with rootful privileges set and try again.',
-      );
-      return;
-    }
+  const isRootful = await machineUtils.isPodmanMachineRootful();
+  if (!isRootful) {
+    await extensionApi.window.showErrorMessage(
+      'The podman machine is not set as rootful. Please recreate the podman machine with rootful privileges set and try again.',
+    );
+    return;
   }
 
   const image = imageData as { name: string; engineId: string; tag: string };
diff --git a/packages/backend/src/machine-utils.spec.ts b/packages/backend/src/machine-utils.spec.ts
index e79a5396..5c997bea 100644
--- a/packages/backend/src/machine-utils.spec.ts
+++ b/packages/backend/src/machine-utils.spec.ts
@@ -84,3 +84,77 @@ test('Check isPodmanMachineRootful functionality', async () => {
   spyReadFile.mockResolvedValue(JSON.stringify({ Rootful: true }));
   await expect(machineUtils.isPodmanMachineRootful()).resolves.toBe(true);
 });
+
+test('Fail isPodmanMachineRootful functionality be false if Rootful does not exist in the root of the object, or in HostUser', async () => {
+  const fakeMachineInfoJSON = {
+    Host: {
+      Arch: 'amd64',
+      CurrentMachine: '',
+      DefaultMachine: '',
+      EventsDir: 'dir1',
+      MachineConfigDir: 'dir2',
+      MachineImageDir: 'dir3',
+      MachineState: '',
+      NumberOfMachines: 5,
+      OS: 'windows',
+      VMType: 'wsl',
+    },
+  };
+
+  vi.spyOn(extensionApi.process, 'exec').mockImplementation(
+    () =>
+      new Promise<extensionApi.RunResult>(resolve => {
+        resolve({ stdout: JSON.stringify(fakeMachineInfoJSON) } as extensionApi.RunResult);
+      }),
+  );
+
+  // Mock existsSync to return true (the "fake" file is there)
+  vi.mock('node:fs');
+  vi.spyOn(fs, 'existsSync').mockImplementation(() => {
+    return true;
+  });
+
+  // Mock the readFile function to return the "fake" file with Rootful not existing
+  const spyReadFile = vi.spyOn(fs.promises, 'readFile');
+
+  // Mock reading the file to have Rootful as true
+  spyReadFile.mockResolvedValue(JSON.stringify({}));
+  await expect(machineUtils.isPodmanMachineRootful()).resolves.toBe(false);
+});
+
+test('Pass true if Rootful is in HostUser', async () => {
+  const fakeMachineInfoJSON = {
+    Host: {
+      Arch: 'amd64',
+      CurrentMachine: '',
+      DefaultMachine: '',
+      EventsDir: 'dir1',
+      MachineConfigDir: 'dir2',
+      MachineImageDir: 'dir3',
+      MachineState: '',
+      NumberOfMachines: 5,
+      OS: 'windows',
+      VMType: 'wsl',
+    },
+  };
+
+  vi.spyOn(extensionApi.process, 'exec').mockImplementation(
+    () =>
+      new Promise<extensionApi.RunResult>(resolve => {
+        resolve({ stdout: JSON.stringify(fakeMachineInfoJSON) } as extensionApi.RunResult);
+      }),
+  );
+
+  // Mock existsSync to return true (the "fake" file is there)
+  vi.mock('node:fs');
+  vi.spyOn(fs, 'existsSync').mockImplementation(() => {
+    return true;
+  });
+
+  // Mock the readFile function to return the "fake" file with Rootful not existing
+  const spyReadFile = vi.spyOn(fs.promises, 'readFile');
+
+  // Mock reading the file to have Rootful as true
+  spyReadFile.mockResolvedValue(JSON.stringify({ HostUser: { Rootful: true } }));
+  await expect(machineUtils.isPodmanMachineRootful()).resolves.toBe(true);
+});
diff --git a/packages/backend/src/machine-utils.ts b/packages/backend/src/machine-utils.ts
index 34e22f91..95b78d5d 100644
--- a/packages/backend/src/machine-utils.ts
+++ b/packages/backend/src/machine-utils.ts
@@ -51,8 +51,17 @@ export async function isPodmanMachineRootful() {
     const machineInfo = await getMachineInfo();
     const machineConfig = await readMachineConfig(machineInfo.Host.MachineConfigDir, machineInfo.Host.CurrentMachine);
 
-    if (machineConfig.Rootful !== undefined) {
-      // Make sure we convert to boolean in case the value is "true", not true.
+    // If you are on Podman Machine 4.9.0 with applehv activated, the rootful key will be located
+    // in the root of the JSON object.
+    // If on 5.0.0, the rootful key will be located in the "HostUser" object.
+    if (machineConfig?.HostUser?.Rootful) {
+      // 5.0.0 check first
+      return Boolean(machineConfig.HostUser.Rootful);
+    } else if (machineConfig?.Rootful) {
+      // 4.9.0 check
+      console.log(
+        'Rootful key found in root object of the machine config file, you could be on Podman Machine 4.9.0, it is recommended to upgrade to 5.0.0.',
+      );
       return Boolean(machineConfig.Rootful);
     } else {
       console.error('No Rootful key found in machine config file, there should be one.');