diff --git a/Core/RetroAchievements.cpp b/Core/RetroAchievements.cpp
index c02c6cd444..4c3ea97710 100644
--- a/Core/RetroAchievements.cpp
+++ b/Core/RetroAchievements.cpp
@@ -89,7 +89,7 @@ rc_client_t *GetClient() {
 }
 
 bool IsLoggedIn() {
-	return rc_client_get_user_info(g_rcClient) != nullptr;
+	return rc_client_get_user_info(g_rcClient) != nullptr && !g_isLoggingIn;
 }
 
 bool EncoreModeActive() {
@@ -129,7 +129,11 @@ bool WarnUserIfChallengeModeActive(const char *message) {
 }
 
 bool IsBlockingExecution() {
-	return g_isIdentifying || g_isLoggingIn;
+	if (g_isLoggingIn || g_isIdentifying) {
+		// Useful for debugging race conditions.
+		// INFO_LOG(ACHIEVEMENTS, "isLoggingIn: %d   isIdentifying: %d", (int)g_isLoggingIn, (int)g_isIdentifying);
+	}
+	return g_isLoggingIn || g_isIdentifying;
 }
 
 static u32 GetGameID() {
@@ -313,6 +317,7 @@ static void event_handler_callback(const rc_client_event_t *event, rc_client_t *
 static void login_token_callback(int result, const char *error_message, rc_client_t *client, void *userdata) {
 	switch (result) {
 	case RC_OK:
+		INFO_LOG(ACHIEVEMENTS, "Successful login by token.");
 		OnAchievementsLoginStateChange();
 		break;
 	case RC_NO_RESPONSE:
@@ -328,7 +333,7 @@ static void login_token_callback(int result, const char *error_message, rc_clien
 	default:
 	{
 		auto ac = GetI18NCategory(I18NCat::ACHIEVEMENTS);
-		ERROR_LOG(ACHIEVEMENTS, "Failure logging in via token: %d, %s", result, error_message);
+		ERROR_LOG(ACHIEVEMENTS, "Callback: Failure logging in via token: %d, %s", result, error_message);
 		g_OSD.Show(OSDType::MESSAGE_WARNING, ac->T("Failed logging in to RetroAchievements"));
 		OnAchievementsLoginStateChange();
 		break;
diff --git a/UI/EmuScreen.cpp b/UI/EmuScreen.cpp
index d32335c663..90aa75199b 100644
--- a/UI/EmuScreen.cpp
+++ b/UI/EmuScreen.cpp
@@ -243,14 +243,14 @@ void EmuScreen::bootGame(const Path &filename) {
 	}
 
 	if (PSP_IsIniting()) {
-		std::string error_string;
+		std::string error_string = "(unknown error)";
 		bootPending_ = !PSP_InitUpdate(&error_string);
 
 		if (!bootPending_) {
 			invalid_ = !PSP_IsInited();
 			if (invalid_) {
 				errorMessage_ = error_string;
-				ERROR_LOG(BOOT, "%s", errorMessage_.c_str());
+				ERROR_LOG(BOOT, "isIniting bootGame error: %s", errorMessage_.c_str());
 				return;
 			}
 			bootComplete();
@@ -331,7 +331,7 @@ void EmuScreen::bootGame(const Path &filename) {
 		bootPending_ = false;
 		invalid_ = true;
 		errorMessage_ = error_string;
-		ERROR_LOG(BOOT, "%s", errorMessage_.c_str());
+		ERROR_LOG(BOOT, "InitStart bootGame error: %s", errorMessage_.c_str());
 	}
 
 	if (PSP_CoreParameter().compat.flags().RequireBufferedRendering && g_Config.bSkipBufferEffects) {
@@ -360,8 +360,9 @@ void EmuScreen::bootComplete() {
 	System_Notify(SystemNotification::BOOT_DONE);
 	System_Notify(SystemNotification::DISASSEMBLY);
 
-	NOTICE_LOG(BOOT, "Loading %s...", PSP_CoreParameter().fileToStart.c_str());
+	NOTICE_LOG(BOOT, "Booted %s...", PSP_CoreParameter().fileToStart.c_str());
 	if (!Achievements::ChallengeModeActive()) {
+		// Don't auto-load savestates in challenge mode.
 		autoLoad();
 	}
 
@@ -1075,6 +1076,8 @@ void EmuScreen::update() {
 	}
 
 	if (bootPending_) {
+		// Keep trying the boot until bootPending_ is lifted.
+		// It may be delayed due to RetroAchievements or any other cause.
 		bootGame(gamePath_);
 	}