diff --git a/entitlements.mac.plist b/entitlements.mac.plist
new file mode 100644
index 00000000..fdba46cc
--- /dev/null
+++ b/entitlements.mac.plist
@@ -0,0 +1,13 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
+<plist version="1.0">
+<dict>
+  <key>com.apple.security.cs.allow-jit</key><true/>
+  <key>com.apple.security.cs.allow-unsigned-executable-memory</key><true/>
+  <key>com.apple.security.cs.allow-dyld-environment-variables</key><true/>
+  <key>com.apple.security.device.audio-input</key><true/>
+  <key>com.apple.security.device.camera</key><true/>
+  <key>com.apple.security.files.user-selected.read-write</key><true/>
+  <key>com.apple.security.network.client</key><true/>
+</dict>
+</plist>
\ No newline at end of file
diff --git a/package.json b/package.json
index b9f4694a..5b5f04e2 100644
--- a/package.json
+++ b/package.json
@@ -52,7 +52,9 @@
     ],
     "mac": {
       "category": "public.app-category.business",
-      "icon": "images/icon.icns"
+      "icon": "images/icon.icns",
+      "entitlements": "entitlements.mac.plist",
+      "entitlementsInherit": "entitlements.mac.plist"
     },
     "win": {
       "icon": "images/icon.ico",
diff --git a/src/app/window-actions.ts b/src/app/window-actions.ts
index 8229b896..5e9b7abf 100644
--- a/src/app/window-actions.ts
+++ b/src/app/window-actions.ts
@@ -144,10 +144,13 @@ export const activate = (windowName: string, shouldFocus: boolean = true): void
 /**
  * Sets always on top property based on isAlwaysOnTop
  *
- * @param shouldSetAlwaysOnTop
- * @param shouldActivateMainWindow
+ * @param shouldSetAlwaysOnTop {boolean} - Whether to enable always on top or not
+ * @param shouldActivateMainWindow {boolean} - Whether to active main window
  */
-export const updateAlwaysOnTop = async (shouldSetAlwaysOnTop: boolean, shouldActivateMainWindow: boolean = true): Promise<void> => {
+export const updateAlwaysOnTop = async (
+    shouldSetAlwaysOnTop: boolean,
+    shouldActivateMainWindow: boolean = true,
+): Promise<void> => {
     logger.info(`window-actions: Should we set always on top? ${shouldSetAlwaysOnTop}!`);
     const browserWins: ICustomBrowserWindow[] = BrowserWindow.getAllWindows() as ICustomBrowserWindow[];
     await config.updateUserConfig({ alwaysOnTop: shouldSetAlwaysOnTop });
@@ -198,6 +201,18 @@ export const handleKeyPress = (key: number): void => {
     }
 };
 
+/**
+ * Sets the window to always on top based
+ * on fullscreen state
+ */
+const setSpecificAlwaysOnTop = () => {
+    const browserWindow = BrowserWindow.getFocusedWindow();
+    if (isMac && browserWindow && windowExists(browserWindow) && browserWindow.isAlwaysOnTop()) {
+        // Set the focused window's always on top level based on fullscreen state
+        browserWindow.setAlwaysOnTop(true, browserWindow.isFullScreen() ? 'modal-panel' : 'floating');
+    }
+};
+
 /**
  * Monitors window actions
  *
@@ -223,6 +238,13 @@ export const monitorWindowActions = (window: BrowserWindow): void => {
     if ((window as ICustomBrowserWindow).winName === apiName.mainWindowName) {
         window.on('restore', throttledWindowRestore);
     }
+
+    // Workaround for an issue with MacOS + AlwaysOnTop
+    // Issue: SDA-1665
+    if (isMac) {
+        window.on('enter-full-screen', setSpecificAlwaysOnTop);
+        window.on('leave-full-screen', setSpecificAlwaysOnTop);
+    }
 };
 
 /**
@@ -246,6 +268,13 @@ export const removeWindowEventListener = (window: BrowserWindow): void => {
 
     window.removeListener('leave-full-screen', throttledWindowChanges);
     window.removeListener('unmaximize', throttledWindowChanges);
+
+    // Workaround for and issue with MacOS + AlwaysOnTop
+    // Issue: SDA-1665
+    if (isMac) {
+        window.removeListener('enter-full-screen', setSpecificAlwaysOnTop);
+        window.removeListener('leave-full-screen', setSpecificAlwaysOnTop);
+    }
 };
 
 /**