diff --git a/DiscordChatExporter.Cli/Commands/Base/ExportCommandBase.cs b/DiscordChatExporter.Cli/Commands/Base/ExportCommandBase.cs
index 6064389d..a237f936 100644
--- a/DiscordChatExporter.Cli/Commands/Base/ExportCommandBase.cs
+++ b/DiscordChatExporter.Cli/Commands/Base/ExportCommandBase.cs
@@ -26,7 +26,11 @@ public abstract class ExportCommandBase : TokenCommandBase
     [CommandOption(
         "output",
         'o',
-        Description = "Output file or directory path. Directory path should end in a slash."
+        Description =
+            "Output file or directory path. " +
+            "If a directory is specified, file names will be generated automatically based on the channel names and other parameters. " +
+            "Directory path should end with a slash to avoid ambiguity. " +
+            "Supports template tokens, see the documentation for more info."
     )]
     public string OutputPath
     {
@@ -58,7 +62,8 @@ public abstract class ExportCommandBase : TokenCommandBase
     [CommandOption(
         "partition",
         'p',
-        Description = "Split output into partitions, each limited to this number of messages (e.g. '100') or file size (e.g. '10mb')."
+        Description =
+            "Split output into partitions, each limited to this number of messages (e.g. '100') or file size (e.g. '10mb')."
     )]
     public PartitionLimit PartitionLimit { get; init; } = PartitionLimit.Null;
 
diff --git a/DiscordChatExporter.Gui/ViewModels/Components/DashboardViewModel.cs b/DiscordChatExporter.Gui/ViewModels/Components/DashboardViewModel.cs
index 47dc6dfc..9f5b5272 100644
--- a/DiscordChatExporter.Gui/ViewModels/Components/DashboardViewModel.cs
+++ b/DiscordChatExporter.Gui/ViewModels/Components/DashboardViewModel.cs
@@ -158,22 +158,27 @@ public class DashboardViewModel : PropertyChangedBase
 
             var exporter = new ChannelExporter(_discord);
 
-            var progresses = Enumerable
-                .Range(0, dialog.Channels!.Count)
-                .Select(_ => _progressMuxer.CreateInput())
+            var channelProgressPairs = dialog
+                .Channels!
+                .Select(c => new
+                {
+                    Channel = c,
+                    Progress = _progressMuxer.CreateInput()
+                })
                 .ToArray();
 
             var successfulExportCount = 0;
 
             await Parallel.ForEachAsync(
-                dialog.Channels.Zip(progresses),
+                channelProgressPairs,
                 new ParallelOptions
                 {
                     MaxDegreeOfParallelism = Math.Max(1, _settingsService.ParallelLimit)
                 },
-                async (tuple, cancellationToken) =>
+                async (pair, cancellationToken) =>
                 {
-                    var (channel, progress) = tuple;
+                    var channel = pair.Channel;
+                    var progress = pair.Progress;
 
                     try
                     {
diff --git a/DiscordChatExporter.Gui/ViewModels/Dialogs/ExportSetupViewModel.cs b/DiscordChatExporter.Gui/ViewModels/Dialogs/ExportSetupViewModel.cs
index d81994a8..6410e7a5 100644
--- a/DiscordChatExporter.Gui/ViewModels/Dialogs/ExportSetupViewModel.cs
+++ b/DiscordChatExporter.Gui/ViewModels/Dialogs/ExportSetupViewModel.cs
@@ -86,15 +86,8 @@ public class ExportSetupViewModel : DialogScreen
 
     public void ToggleAdvancedSection() => IsAdvancedSectionDisplayed = !IsAdvancedSectionDisplayed;
 
-    public void Confirm()
+    public void ShowOutputPathPrompt()
     {
-        // Persist preferences
-        _settingsService.LastExportFormat = SelectedFormat;
-        _settingsService.LastPartitionLimitValue = PartitionLimitValue;
-        _settingsService.LastMessageFilterValue = MessageFilterValue;
-        _settingsService.LastShouldDownloadAssets = ShouldDownloadAssets;
-
-        // If single channel - prompt file path
         if (IsSingleChannel)
         {
             var defaultFileName = ExportRequest.GetDefaultOutputFileName(
@@ -105,20 +98,26 @@ public class ExportSetupViewModel : DialogScreen
                 Before?.Pipe(Snowflake.FromDate)
             );
 
-            // Filter
-            var ext = SelectedFormat.GetFileExtension();
-            var filter = $"{ext.ToUpperInvariant()} files|*.{ext}";
+            var extension = SelectedFormat.GetFileExtension();
+            var filter = $"{extension.ToUpperInvariant()} files|*.{extension}";
 
             OutputPath = _dialogManager.PromptSaveFilePath(filter, defaultFileName);
         }
-        // If multiple channels - prompt dir path
         else
         {
             OutputPath = _dialogManager.PromptDirectoryPath();
         }
+    }
 
-        if (string.IsNullOrWhiteSpace(OutputPath))
-            return;
+    public bool CanConfirm => !string.IsNullOrWhiteSpace(OutputPath);
+
+    public void Confirm()
+    {
+        // Persist preferences
+        _settingsService.LastExportFormat = SelectedFormat;
+        _settingsService.LastPartitionLimitValue = PartitionLimitValue;
+        _settingsService.LastMessageFilterValue = MessageFilterValue;
+        _settingsService.LastShouldDownloadAssets = ShouldDownloadAssets;
 
         Close(true);
     }
diff --git a/DiscordChatExporter.Gui/Views/Dialogs/ExportSetupView.xaml b/DiscordChatExporter.Gui/Views/Dialogs/ExportSetupView.xaml
index 7ee8144b..0267697b 100644
--- a/DiscordChatExporter.Gui/Views/Dialogs/ExportSetupView.xaml
+++ b/DiscordChatExporter.Gui/Views/Dialogs/ExportSetupView.xaml
@@ -76,6 +76,86 @@
             BorderThickness="0,1">
             <ScrollViewer HorizontalScrollBarVisibility="Disabled" VerticalScrollBarVisibility="Auto">
                 <StackPanel>
+                    <!--  Output path  -->
+                    <Grid>
+                        <Grid.ColumnDefinitions>
+                            <ColumnDefinition Width="*" />
+                            <ColumnDefinition Width="Auto" />
+                        </Grid.ColumnDefinitions>
+                        <TextBox
+                            Grid.Column="0"
+                            Margin="16,8,8,8"
+                            materialDesign:HintAssist.Hint="Output path"
+                            materialDesign:HintAssist.IsFloating="True"
+                            Style="{DynamicResource MaterialDesignOutlinedTextBox}"
+                            Text="{Binding OutputPath}">
+                            <TextBox.ToolTip>
+                                <TextBlock>
+                                    <Run Text="Output file or directory path." />
+                                    <Run Text="If a directory is specified, file names will be generated automatically based on the channel names and other parameters." />
+                                    <Run Text="Directory path should end with a slash to avoid ambiguity." />
+                                    <LineBreak />
+                                    <LineBreak />
+                                    <Run Text="Available template tokens:" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%g" />
+                                    <Run Text="— guild ID" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%G" />
+                                    <Run Text="— guild name" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%t" />
+                                    <Run Text="— category ID" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%T" />
+                                    <Run Text="— category name" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%c" />
+                                    <Run Text="— channel ID" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%C" />
+                                    <Run Text="— channel name" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%p" />
+                                    <Run Text="— channel position" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%P" />
+                                    <Run Text="— category position" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%a" />
+                                    <Run Text="— after date" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%b" />
+                                    <Run Text="— before date" />
+                                    <LineBreak />
+                                    <Run FontWeight="SemiBold" Text="%d" />
+                                    <Run Text="— current date" />
+                                </TextBlock>
+                            </TextBox.ToolTip>
+                        </TextBox>
+                        <Button
+                            Grid.Column="1"
+                            Height="48"
+                            Margin="0,8,16,8"
+                            Command="{s:Action ShowOutputPathPrompt}"
+                            Style="{DynamicResource MaterialDesignOutlinedButton}">
+                            <materialDesign:PackIcon Width="24" Height="24">
+                                <materialDesign:PackIcon.Style>
+                                    <Style TargetType="{x:Type materialDesign:PackIcon}">
+                                        <Style.Triggers>
+                                            <DataTrigger Binding="{Binding IsSingleChannel}" Value="True">
+                                                <Setter Property="Kind" Value="FileFind" />
+                                            </DataTrigger>
+                                            <DataTrigger Binding="{Binding IsSingleChannel}" Value="False">
+                                                <Setter Property="Kind" Value="FolderSearch" />
+                                            </DataTrigger>
+                                        </Style.Triggers>
+                                    </Style>
+                                </materialDesign:PackIcon.Style>
+                            </materialDesign:PackIcon>
+                        </Button>
+                    </Grid>
+
                     <!--  Format  -->
                     <ComboBox
                         Margin="16,8"
@@ -84,7 +164,8 @@
                         IsReadOnly="True"
                         ItemsSource="{Binding AvailableFormats}"
                         SelectedItem="{Binding SelectedFormat}"
-                        Style="{DynamicResource MaterialDesignOutlinedComboBox}">
+                        Style="{DynamicResource MaterialDesignOutlinedComboBox}"
+                        ToolTip="Export format">
                         <ComboBox.ItemTemplate>
                             <DataTemplate>
                                 <TextBlock Text="{Binding Converter={x:Static converters:ExportFormatToStringConverter.Instance}, ConverterCulture={x:Static globalization:CultureInfo.CurrentCulture}}" />
diff --git a/DiscordChatExporter.Gui/Views/Dialogs/SettingsView.xaml b/DiscordChatExporter.Gui/Views/Dialogs/SettingsView.xaml
index 66cc9fa0..20159486 100644
--- a/DiscordChatExporter.Gui/Views/Dialogs/SettingsView.xaml
+++ b/DiscordChatExporter.Gui/Views/Dialogs/SettingsView.xaml
@@ -40,7 +40,7 @@
                         <TextBlock
                             VerticalAlignment="Center"
                             DockPanel.Dock="Left"
-                            Text="Auto-updates" />
+                            Text="Auto-update" />
                         <ToggleButton
                             VerticalAlignment="Center"
                             DockPanel.Dock="Right"
@@ -75,7 +75,7 @@
                         <TextBlock
                             VerticalAlignment="Center"
                             DockPanel.Dock="Left"
-                            Text="Save token" />
+                            Text="Persist token" />
                         <ToggleButton
                             VerticalAlignment="Center"
                             DockPanel.Dock="Right"