Fix login loop (#6402)

frontend/editor/src-tauri/src/commands/auth.rs

@@ -1,7 +1,7 @@
 use keyring::{Entry};
 use serde::{Deserialize, Serialize};
 use std::sync::{Arc, Mutex};
-use tauri::AppHandle;
+use tauri::{AppHandle, Runtime};
 use tauri_plugin_store::StoreExt;
 use tiny_http::{Response, Server};
 use sha2::{Sha256, Digest};
@@ -18,6 +18,9 @@ const KEYRING_SERVICE: &str = "stirling-pdf";
 const KEYRING_TOKEN_KEY: &str = "auth-token";
 const KEYRING_REFRESH_TOKEN_KEY: &str = "refresh-token";
 
+pub const TOKENS_STORE_FILE_FOR_TESTS: &str = TOKENS_STORE_FILE;
+pub const REFRESH_TOKEN_STORE_KEY_FOR_TESTS: &str = REFRESH_TOKEN_STORE_KEY;
+
 #[derive(Debug, Serialize, Deserialize, Clone)]
 pub struct UserInfo {
     pub username: String,
@@ -25,6 +28,9 @@ pub struct UserInfo {
 }
 
 fn get_keyring_entry() -> Result<Entry, String> {
+    if std::env::var("STIRLING_PDF_TEST_FORCE_AUTH_KEYRING_FAIL").is_ok() {
+        return Err("Forced keyring failure for tests".to_string());
+    }
     log::debug!("Creating keyring entry with service='{}' username='{}'", KEYRING_SERVICE, KEYRING_TOKEN_KEY);
     let entry = Entry::new(KEYRING_SERVICE, KEYRING_TOKEN_KEY)
         .map_err(|e| {
@@ -35,11 +41,28 @@ fn get_keyring_entry() -> Result<Entry, String> {
     Ok(entry)
 }
 
-fn get_refresh_token_keyring_entry() -> Result<Entry, String> {
+pub fn get_refresh_token_keyring_entry() -> Result<Entry, String> {
+    if std::env::var("STIRLING_PDF_TEST_FORCE_REFRESH_KEYRING_FAIL").is_ok() {
+        return Err("Forced keyring failure for tests".to_string());
+    }
     Entry::new(KEYRING_SERVICE, KEYRING_REFRESH_TOKEN_KEY)
         .map_err(|e| format!("Failed to access keyring: {}", e))
 }
 
+/// Returns Ok(true) when keyring round-tripped the token; Ok(false) otherwise (caller must fall through to disk).
+pub fn try_save_refresh_token_to_keyring(token: &str) -> Result<bool, String> {
+    match get_refresh_token_keyring_entry() {
+        Ok(entry) => match entry.set_password(token) {
+            Ok(_) => match entry.get_password() {
+                Ok(saved) if saved == token => Ok(true),
+                _ => Ok(false),
+            },
+            Err(_) => Ok(false),
+        },
+        Err(_) => Ok(false),
+    }
+}
+
 #[tauri::command]
 pub async fn save_auth_token(app_handle: AppHandle, token: String) -> Result<(), String> {
     let trimmed = token.trim();
@@ -172,31 +195,30 @@ pub async fn clear_auth_token(app_handle: AppHandle) -> Result<(), String> {
 }
 
 #[tauri::command]
-pub async fn save_refresh_token(app_handle: AppHandle, token: String) -> Result<(), String> {
+pub async fn save_refresh_token<R: Runtime>(app_handle: AppHandle<R>, token: String) -> Result<(), String> {
     log::info!("Saving refresh token - trying keyring first");
 
-    let entry = get_refresh_token_keyring_entry()?;
+    match try_save_refresh_token_to_keyring(&token) {
-
+        Ok(true) => {
-    // Try keyring (works in production with code signing)
+            // Clear any stale fallback copy so the keyring stays authoritative.
-    match entry.set_password(&token) {
+            if let Ok(store) = app_handle.store(TOKENS_STORE_FILE) {
-        Ok(_) => {
+                if store.get(REFRESH_TOKEN_STORE_KEY).is_some() {
-            // Verify it persists (fails in unsigned dev builds)
+                    store.delete(REFRESH_TOKEN_STORE_KEY);
-            match entry.get_password() {
+                    let _ = store.save();
-                Ok(saved) if saved == token => {
-                    log::info!("✅ Refresh token saved to keyring (production mode)");
-                    return Ok(());
-                }
-                _ => {
-                    log::info!("Keyring doesn't persist - using Tauri Store fallback (dev mode)");
                 }
             }
+            log::info!("Refresh token saved to keyring");
+            return Ok(());
+        }
+        Ok(false) => {
+            log::info!("Keyring did not persist refresh token - using Tauri Store fallback");
         }
         Err(e) => {
-            log::info!("Keyring failed: {} - using Tauri Store fallback", e);
+            log::info!("Keyring error for refresh token: {} - using Tauri Store fallback", e);
         }
     }
 
-    // Fallback to Tauri Store (dev mode without code signing)
+    // Fallback to Tauri Store (dev mode without code signing, or restricted environments)
     let store = app_handle
         .store(TOKENS_STORE_FILE)
         .map_err(|e| format!("Failed to access tokens store: {}", e))?;
@@ -211,28 +233,33 @@ pub async fn save_refresh_token(app_handle: AppHandle, token: String) -> Result<
         .save()
         .map_err(|e| format!("Failed to save tokens store: {}", e))?;
 
-    log::info!("✅ Refresh token saved to Tauri Store (fallback)");
+    log::info!("Refresh token saved to Tauri Store (fallback)");
     Ok(())
 }
 
 #[tauri::command]
-pub async fn get_refresh_token(app_handle: AppHandle) -> Result<Option<String>, String> {
+pub async fn get_refresh_token<R: Runtime>(app_handle: AppHandle<R>) -> Result<Option<String>, String> {
-    // Try keyring first (production)
+    // Try keyring first (production / unrestricted environments). Any failure -
-    let entry = get_refresh_token_keyring_entry()?;
+    // including entry creation - falls through to the Tauri Store fallback below.
-    match entry.get_password() {
+    match get_refresh_token_keyring_entry() {
-        Ok(token) => {
+        Ok(entry) => match entry.get_password() {
-            log::info!("✅ Refresh token retrieved from keyring");
+            Ok(token) => {
-            return Ok(Some(token));
+                log::info!("Refresh token retrieved from keyring");
-        }
+                return Ok(Some(token));
-        Err(keyring::Error::NoEntry) => {
+            }
-            log::debug!("No token in keyring, trying Tauri Store");
+            Err(keyring::Error::NoEntry) => {
-        }
+                log::debug!("No refresh token in keyring, trying Tauri Store");
+            }
+            Err(e) => {
+                log::warn!("Keyring error reading refresh token: {} - trying Tauri Store", e);
+            }
+        },
         Err(e) => {
-            log::warn!("Keyring error: {} - trying Tauri Store", e);
+            log::warn!("Keyring entry unavailable for refresh token: {} - trying Tauri Store", e);
         }
     }
 
-    // Fallback to Tauri Store (dev)
+    // Fallback to Tauri Store (dev or restricted environments)
     let store = app_handle
         .store(TOKENS_STORE_FILE)
         .map_err(|e| format!("Failed to access tokens store: {}", e))?;
@@ -242,7 +269,7 @@ pub async fn get_refresh_token(app_handle: AppHandle) -> Result<Option<String>,
         .and_then(|v| serde_json::from_value(v.clone()).ok());
 
     if token.is_some() {
-        log::info!("✅ Refresh token retrieved from Tauri Store");
+        log::info!("Refresh token retrieved from Tauri Store");
     } else {
         log::info!("No refresh token found");
     }
@@ -251,18 +278,26 @@ pub async fn get_refresh_token(app_handle: AppHandle) -> Result<Option<String>,
 }
 
 #[tauri::command]
-pub async fn clear_refresh_token(app_handle: AppHandle) -> Result<(), String> {
+pub async fn clear_refresh_token<R: Runtime>(app_handle: AppHandle<R>) -> Result<(), String> {
     log::info!("Clearing refresh token from all storage");
 
-    // Clear from keyring
+    // Best-effort keyring clear; never blocks disk clear.
-    let entry = get_refresh_token_keyring_entry()?;
+    match get_refresh_token_keyring_entry() {
-    match entry.delete_credential() {
+        Ok(entry) => match entry.delete_credential() {
-        Ok(_) => log::info!("Cleared from keyring"),
+            Ok(_) | Err(keyring::Error::NoEntry) => {}
-        Err(keyring::Error::NoEntry) => log::debug!("Not in keyring"),
+            Err(e) => {
-        Err(e) => log::warn!("Keyring clear error: {}", e),
+                log::warn!("Failed to delete keyring refresh token: {}. Attempting overwrite with empty token.", e);
+                if let Err(e2) = entry.set_password("") {
+                    log::warn!("Failed to overwrite keyring refresh token: {}", e2);
+                }
+            }
+        },
+        Err(e) => {
+            log::warn!("Keyring entry unavailable while clearing refresh token: {} - clearing Tauri Store fallback only", e);
+        }
     }
 
-    // Clear from Tauri Store
+    // Clear from Tauri Store fallback
     let store = app_handle
         .store(TOKENS_STORE_FILE)
         .map_err(|e| format!("Failed to access tokens store: {}", e))?;
@@ -273,7 +308,7 @@ pub async fn clear_refresh_token(app_handle: AppHandle) -> Result<(), String> {
         .save()
         .map_err(|e| format!("Failed to save tokens store: {}", e))?;
 
-    log::info!("✅ Refresh token cleared");
+    log::info!("Refresh token cleared");
     Ok(())
 }
 

frontend/editor/src-tauri/src/lib.rs

@@ -1,7 +1,7 @@
 use tauri::{AppHandle, Emitter, Manager, RunEvent, WindowEvent};
 
 mod utils;
-mod commands;
+pub mod commands;
 mod state;
 
 use commands::{

frontend/src-tauri/tests/refresh_token_fallback.rs

@@ -0,0 +1,94 @@
+//! Asserts the refresh-token keyring helper falls through (Ok(false))
+//! instead of bailing (Err) when keyring access fails. This was the
+//! original login-loop bug.
+
+use app_lib::commands::auth::{
+    get_refresh_token_keyring_entry, try_save_refresh_token_to_keyring,
+    REFRESH_TOKEN_STORE_KEY_FOR_TESTS, TOKENS_STORE_FILE_FOR_TESTS,
+};
+use serde_json::json;
+
+const ENV_FORCE_FAIL: &str = "STIRLING_PDF_TEST_FORCE_REFRESH_KEYRING_FAIL";
+
+// Single test fn — env var is process-global; parallel tests would race.
+#[test]
+fn refresh_token_fallback_proof() {
+    // ===== Step 1: env-var injection forces keyring entry-creation to Err =====
+    std::env::set_var(ENV_FORCE_FAIL, "1");
+
+    let entry_result = get_refresh_token_keyring_entry();
+    assert!(
+        entry_result.is_err(),
+        "with {} set, get_refresh_token_keyring_entry must return Err",
+        ENV_FORCE_FAIL
+    );
+    let err_msg = entry_result.err().unwrap();
+    assert!(
+        err_msg.contains("Forced keyring failure for tests"),
+        "expected forced-failure marker; got: {}",
+        err_msg
+    );
+
+    // ===== Step 2: the bug-fix proof =====
+    // Original bug: `let entry = get_refresh_token_keyring_entry()?;` would
+    // propagate Err and short-circuit save_refresh_token, never reaching the
+    // disk-store fallback. Fixed behaviour: the same keyring failure must be
+    // converted into a "fall through" signal (Ok(false)), NOT propagated as Err.
+    let outcome = try_save_refresh_token_to_keyring("test-token-xyz-456");
+    assert!(
+        matches!(outcome, Ok(false)),
+        "REGRESSION: keyring entry-creation failure must convert to Ok(false) \
+         so save_refresh_token falls through to the disk store. Got {:?}. \
+         This means the function would short-circuit and the user's refresh \
+         token would never be persisted - exactly the original login-loop bug.",
+        outcome
+    );
+
+    std::env::remove_var(ENV_FORCE_FAIL);
+
+    // ===== Step 3: env-var unset does NOT carry the forced-failure marker =====
+    let result_unset = get_refresh_token_keyring_entry();
+    if let Err(e) = &result_unset {
+        assert!(
+            !e.contains("Forced keyring failure for tests"),
+            "with {} unset, error must NOT contain forced-failure marker; got: {}",
+            ENV_FORCE_FAIL,
+            e
+        );
+    }
+
+    // ===== Step 4: disk-fallback JSON round-trips =====
+    // tauri_plugin_store writes via serde_json::to_vec_pretty(&HashMap<String,
+    // JsonValue>). Reproduce that format and verify it round-trips, proving
+    // the file save_refresh_token's disk fallback writes is readable by
+    // get_refresh_token's disk fallback.
+    let tmp = std::env::temp_dir().join(format!(
+        "stirling_pdf_refresh_token_test_{}.json",
+        std::process::id()
+    ));
+    let token = "test-refresh-token-disk-roundtrip-abc-123";
+    let mut map = std::collections::HashMap::<String, serde_json::Value>::new();
+    map.insert(REFRESH_TOKEN_STORE_KEY_FOR_TESTS.to_string(), json!(token));
+    let bytes = serde_json::to_vec_pretty(&map).expect("serialize tokens map");
+    std::fs::write(&tmp, &bytes).expect("write tokens file");
+
+    let read_bytes = std::fs::read(&tmp).expect("read tokens file");
+    let read_map: std::collections::HashMap<String, serde_json::Value> =
+        serde_json::from_slice(&read_bytes).expect("parse tokens json");
+    let retrieved: Option<String> = read_map
+        .get(REFRESH_TOKEN_STORE_KEY_FOR_TESTS)
+        .and_then(|v| serde_json::from_value(v.clone()).ok());
+
+    let _ = std::fs::remove_file(&tmp);
+
+    assert_eq!(
+        retrieved,
+        Some(token.to_string()),
+        "disk-fallback JSON format must round-trip the refresh token (file: {})",
+        tmp.display()
+    );
+
+    // ===== Step 5: constants match production strings =====
+    assert_eq!(TOKENS_STORE_FILE_FOR_TESTS, "tokens.json");
+    assert_eq!(REFRESH_TOKEN_STORE_KEY_FOR_TESTS, "refresh_token");
+}