diff --git a/templates/login.html b/templates/login.html
index a4f8ea1..9cc37df 100644
--- a/templates/login.html
+++ b/templates/login.html
@@ -295,16 +295,34 @@
             };
 
             let msalInstance = null;
+            let msalReady = false;
 
-            // Initialize MSAL
+            // Initialize MSAL and handle any pending redirects
             async function initMsal() {
-                msalInstance = new msal.PublicClientApplication(msalConfig);
-                await msalInstance.initialize();
+                try {
+                    msalInstance = new msal.PublicClientApplication(msalConfig);
+                    await msalInstance.initialize();
+
+                    // Handle any pending redirect (in case user lands on login page after OAuth)
+                    const response = await msalInstance.handleRedirectPromise();
+                    if (response && response.accessToken) {
+                        // User completed auth, send token to server
+                        await sendTokenToServer(response.accessToken);
+                        return;
+                    }
+
+                    msalReady = true;
+                } catch (error) {
+                    console.error("MSAL init error:", error);
+                    // Clear any stuck interaction state
+                    sessionStorage.clear();
+                    msalReady = true;
+                }
             }
             initMsal();
 
             async function loginWithMicrosoft() {
-                if (!msalInstance) {
+                if (!msalReady) {
                     alert("Please wait, authentication is initializing...");
                     return;
                 }
@@ -315,7 +333,29 @@
                     await msalInstance.loginRedirect(loginRequest);
                 } catch (error) {
                     console.error("Login error:", error);
-                    alert("Login failed: " + error.message);
+                    if (error.errorCode === "interaction_in_progress") {
+                        // Clear stuck state and retry
+                        sessionStorage.clear();
+                        alert("Please click the button again.");
+                    } else {
+                        alert("Login failed: " + error.message);
+                    }
+                }
+            }
+
+            async function sendTokenToServer(accessToken) {
+                try {
+                    const response = await fetch("/solventum-image-metadata/auth/token", {
+                        method: "POST",
+                        headers: { "Content-Type": "application/json" },
+                        body: JSON.stringify({ access_token: accessToken })
+                    });
+                    const data = await response.json();
+                    if (data.success && data.redirect) {
+                        window.location.href = data.redirect;
+                    }
+                } catch (error) {
+                    console.error("Server error:", error);
                 }
             }
         </script>