diff --git a/UI/window-basic-filters.cpp b/UI/window-basic-filters.cpp
index 8db101946..fa2ef9906 100644
--- a/UI/window-basic-filters.cpp
+++ b/UI/window-basic-filters.cpp
@@ -434,7 +434,7 @@ void OBSBasicFilters::AddNewFilter(const char *id)
 			return;
 
 		if (name.empty()) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			AddNewFilter(id);
@@ -444,7 +444,7 @@ void OBSBasicFilters::AddNewFilter(const char *id)
 		existing_filter = obs_source_get_filter_by_name(source,
 				name.c_str());
 		if (existing_filter) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NameExists.Title"),
 					QTStr("NameExists.Text"));
 			obs_source_release(existing_filter);
diff --git a/UI/window-basic-main-outputs.cpp b/UI/window-basic-main-outputs.cpp
index 90a38c8db..6b3e46fc6 100644
--- a/UI/window-basic-main-outputs.cpp
+++ b/UI/window-basic-main-outputs.cpp
@@ -63,7 +63,8 @@ static void OBSStopStreaming(void *data, calldata_t *params)
 	output->delayActive = false;
 	os_atomic_set_bool(&streaming_active, false);
 	QMetaObject::invokeMethod(output->main,
-			"StreamingStop", Q_ARG(int, code), Q_ARG(QString, arg_last_error));
+			"StreamingStop", Q_ARG(int, code),
+			Q_ARG(QString, arg_last_error));
 }
 
 static void OBSStartRecording(void *data, calldata_t *params)
@@ -81,11 +82,15 @@ static void OBSStopRecording(void *data, calldata_t *params)
 {
 	BasicOutputHandler *output = static_cast<BasicOutputHandler*>(data);
 	int code = (int)calldata_int(params, "code");
+	const char *last_error = calldata_string(params, "last_error");
+
+	QString arg_last_error = QString::fromUtf8(last_error);
 
 	output->recordingActive = false;
 	os_atomic_set_bool(&recording_active, false);
 	QMetaObject::invokeMethod(output->main,
-			"RecordingStop", Q_ARG(int, code));
+			"RecordingStop", Q_ARG(int, code),
+			Q_ARG(QString, arg_last_error));
 
 	UNUSED_PARAMETER(params);
 }
@@ -891,7 +896,7 @@ bool SimpleOutput::ConfigureRecording(bool updateReplayBuffer)
 
 	if (!dir) {
 		if (main->isVisible())
-			OBSMessageBox::information(main,
+			OBSMessageBox::warning(main,
 					QTStr("Output.BadPath.Title"),
 					QTStr("Output.BadPath.Text"));
 		else
@@ -1658,7 +1663,7 @@ bool AdvancedOutput::StartRecording()
 
 		if (!dir) {
 			if (main->isVisible())
-				OBSMessageBox::information(main,
+				OBSMessageBox::warning(main,
 						QTStr("Output.BadPath.Title"),
 						QTStr("Output.BadPath.Text"));
 			else
@@ -1758,7 +1763,7 @@ bool AdvancedOutput::StartReplayBuffer()
 
 		if (!dir) {
 			if (main->isVisible())
-				OBSMessageBox::information(main,
+				OBSMessageBox::warning(main,
 						QTStr("Output.BadPath.Title"),
 						QTStr("Output.BadPath.Text"));
 			else
diff --git a/UI/window-basic-main-profiles.cpp b/UI/window-basic-main-profiles.cpp
index 24640eee1..aa512d540 100644
--- a/UI/window-basic-main-profiles.cpp
+++ b/UI/window-basic-main-profiles.cpp
@@ -107,13 +107,13 @@ static bool GetProfileName(QWidget *parent, std::string &name,
 			return false;
 		}
 		if (name.empty()) {
-			OBSMessageBox::information(parent,
+			OBSMessageBox::warning(parent,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			continue;
 		}
 		if (ProfileExists(name.c_str())) {
-			OBSMessageBox::information(parent,
+			OBSMessageBox::warning(parent,
 					QTStr("NameExists.Title"),
 					QTStr("NameExists.Text"));
 			continue;
@@ -526,7 +526,7 @@ void OBSBasic::on_actionImportProfile_triggered()
 					profileDir + "/recordEncoder.json");
 			RefreshProfiles();
 		} else {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("Basic.MainMenu.Profile.Import"),
 					QTStr("Basic.MainMenu.Profile.Exists"));
 		}
diff --git a/UI/window-basic-main-scene-collections.cpp b/UI/window-basic-main-scene-collections.cpp
index 56661ce0a..84da0f3e4 100644
--- a/UI/window-basic-main-scene-collections.cpp
+++ b/UI/window-basic-main-scene-collections.cpp
@@ -114,13 +114,13 @@ static bool GetSceneCollectionName(QWidget *parent, std::string &name,
 			return false;
 		}
 		if (name.empty()) {
-			OBSMessageBox::information(parent,
+			OBSMessageBox::warning(parent,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			continue;
 		}
 		if (SceneCollectionExists(name.c_str())) {
-			OBSMessageBox::information(parent,
+			OBSMessageBox::warning(parent,
 					QTStr("NameExists.Title"),
 					QTStr("NameExists.Text"));
 			continue;
diff --git a/UI/window-basic-main-transitions.cpp b/UI/window-basic-main-transitions.cpp
index 5d3530122..939910930 100644
--- a/UI/window-basic-main-transitions.cpp
+++ b/UI/window-basic-main-transitions.cpp
@@ -453,7 +453,7 @@ void OBSBasic::AddTransition()
 
 	if (accepted) {
 		if (name.empty()) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			AddTransition();
@@ -462,7 +462,7 @@ void OBSBasic::AddTransition()
 
 		source = FindTransition(name.c_str());
 		if (source) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NameExists.Title"),
 					QTStr("NameExists.Text"));
 
@@ -559,7 +559,7 @@ void OBSBasic::RenameTransition()
 
 	if (accepted) {
 		if (name.empty()) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			RenameTransition();
@@ -568,7 +568,7 @@ void OBSBasic::RenameTransition()
 
 		source = FindTransition(name.c_str());
 		if (source) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NameExists.Title"),
 					QTStr("NameExists.Text"));
 
diff --git a/UI/window-basic-main.cpp b/UI/window-basic-main.cpp
index 8909133ab..0af17baa7 100644
--- a/UI/window-basic-main.cpp
+++ b/UI/window-basic-main.cpp
@@ -2790,7 +2790,7 @@ void OBSBasic::MixerRenameSource()
 			return;
 
 		if (name.empty()) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			continue;
@@ -2800,7 +2800,7 @@ void OBSBasic::MixerRenameSource()
 		obs_source_release(sourceTest);
 
 		if (sourceTest) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NameExists.Title"),
 					QTStr("NameExists.Text"));
 			continue;
@@ -3165,7 +3165,7 @@ void OBSBasic::DuplicateSelectedScene()
 			return;
 
 		if (name.empty()) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			continue;
@@ -3173,7 +3173,7 @@ void OBSBasic::DuplicateSelectedScene()
 
 		obs_source_t *source = obs_get_source_by_name(name.c_str());
 		if (source) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NameExists.Title"),
 					QTStr("NameExists.Text"));
 
@@ -4109,7 +4109,7 @@ void OBSBasic::on_actionAddScene_triggered()
 
 	if (accepted) {
 		if (name.empty()) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			on_actionAddScene_triggered();
@@ -4118,7 +4118,7 @@ void OBSBasic::on_actionAddScene_triggered()
 
 		obs_source_t *source = obs_get_source_by_name(name.c_str());
 		if (source) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NameExists.Title"),
 					QTStr("NameExists.Text"));
 
@@ -4869,7 +4869,7 @@ void OBSBasic::logUploadFinished(const QString &text, const QString &error)
 	ui->menuLogFiles->setEnabled(true);
 
 	if (text.isEmpty()) {
-		OBSMessageBox::information(this,
+		OBSMessageBox::critical(this,
 				QTStr("LogReturnDialog.ErrorUploadingLog"),
 				error);
 		return;
@@ -4898,11 +4898,11 @@ static void RenameListItem(OBSBasic *parent, QListWidget *listWidget,
 		listItem->setText(QT_UTF8(prevName));
 
 		if (foundSource) {
-			OBSMessageBox::information(parent,
+			OBSMessageBox::warning(parent,
 				QTStr("NameExists.Title"),
 				QTStr("NameExists.Text"));
 		} else if (name.empty()) {
-			OBSMessageBox::information(parent,
+			OBSMessageBox::warning(parent,
 				QTStr("NoNameEntered.Title"),
 				QTStr("NoNameEntered.Text"));
 		}
@@ -5363,7 +5363,7 @@ void OBSBasic::RecordingStart()
 	blog(LOG_INFO, RECORDING_START);
 }
 
-void OBSBasic::RecordingStop(int code)
+void OBSBasic::RecordingStop(int code, QString last_error)
 {
 	ui->statusbar->RecordingStopped();
 	ui->recordButton->setText(QTStr("Basic.Main.StartRecording"));
@@ -5375,19 +5375,32 @@ void OBSBasic::RecordingStop(int code)
 	blog(LOG_INFO, RECORDING_STOP);
 
 	if (code == OBS_OUTPUT_UNSUPPORTED && isVisible()) {
-		OBSMessageBox::information(this,
+		OBSMessageBox::critical(this,
 				QTStr("Output.RecordFail.Title"),
 				QTStr("Output.RecordFail.Unsupported"));
 
 	} else if (code == OBS_OUTPUT_NO_SPACE && isVisible()) {
-		OBSMessageBox::information(this,
+		OBSMessageBox::warning(this,
 				QTStr("Output.RecordNoSpace.Title"),
 				QTStr("Output.RecordNoSpace.Msg"));
 
 	} else if (code != OBS_OUTPUT_SUCCESS && isVisible()) {
-		OBSMessageBox::information(this,
+
+		const char *errorDescription;
+		DStr errorMessage;
+		bool use_last_error = true;
+
+		errorDescription = Str("Output.RecordError.Msg");
+
+		if (use_last_error && !last_error.isEmpty())
+			dstr_printf(errorMessage, "%s\n\n%s", errorDescription,
+				QT_TO_UTF8(last_error));
+		else
+			dstr_copy(errorMessage, errorDescription);
+
+		OBSMessageBox::critical(this,
 				QTStr("Output.RecordError.Title"),
-				QTStr("Output.RecordError.Msg"));
+				QT_UTF8(errorMessage));
 
 	} else if (code == OBS_OUTPUT_UNSUPPORTED && !isVisible()) {
 		SysTrayNotify(QTStr("Output.RecordFail.Unsupported"),
@@ -5528,17 +5541,17 @@ void OBSBasic::ReplayBufferStop(int code)
 	blog(LOG_INFO, REPLAY_BUFFER_STOP);
 
 	if (code == OBS_OUTPUT_UNSUPPORTED && isVisible()) {
-		OBSMessageBox::information(this,
+		OBSMessageBox::critical(this,
 				QTStr("Output.RecordFail.Title"),
 				QTStr("Output.RecordFail.Unsupported"));
 
 	} else if (code == OBS_OUTPUT_NO_SPACE && isVisible()) {
-		OBSMessageBox::information(this,
+		OBSMessageBox::warning(this,
 				QTStr("Output.RecordNoSpace.Title"),
 				QTStr("Output.RecordNoSpace.Msg"));
 
 	} else if (code != OBS_OUTPUT_SUCCESS && isVisible()) {
-		OBSMessageBox::information(this,
+		OBSMessageBox::critical(this,
 				QTStr("Output.RecordError.Title"),
 				QTStr("Output.RecordError.Msg"));
 
diff --git a/UI/window-basic-main.hpp b/UI/window-basic-main.hpp
index 3495dae26..a94215341 100644
--- a/UI/window-basic-main.hpp
+++ b/UI/window-basic-main.hpp
@@ -438,7 +438,7 @@ public slots:
 
 	void RecordingStart();
 	void RecordStopping();
-	void RecordingStop(int code);
+	void RecordingStop(int code, QString last_error);
 
 	void StartReplayBuffer();
 	void StopReplayBuffer();
diff --git a/UI/window-basic-source-select.cpp b/UI/window-basic-source-select.cpp
index f2bf21b97..171dc64ef 100644
--- a/UI/window-basic-source-select.cpp
+++ b/UI/window-basic-source-select.cpp
@@ -215,7 +215,7 @@ void OBSBasicSourceSelect::on_buttonBox_accepted()
 		AddExisting(QT_TO_UTF8(item->text()), visible, false);
 	} else {
 		if (ui->sourceName->text().isEmpty()) {
-			OBSMessageBox::information(this,
+			OBSMessageBox::warning(this,
 					QTStr("NoNameEntered.Title"),
 					QTStr("NoNameEntered.Text"));
 			return;