diff --git a/ImageDescriber.Test/MenuTests.cs b/ImageDescriber.Test/MenuTests.cs
index 4d488d9..1242090 100644
--- a/ImageDescriber.Test/MenuTests.cs
+++ b/ImageDescriber.Test/MenuTests.cs
@@ -3,6 +3,8 @@
 namespace ktsu.ImageDescriber.Tests;
 
 using ktsu.ImageDescriber.Verbs;
+using ktsu.Semantics.Paths;
+using ktsu.Semantics.Strings;
 
 [TestClass]
 public class MenuTests
@@ -87,4 +89,95 @@ public void PromptMenuStopsAtEndOfInput()
 
 		Assert.AreEqual("Only", string.Join(",", ran));
 	}
+
+	[TestMethod]
+	public void ExportRunWithoutAnOutputPathAsksForOne()
+	{
+		string outputFile = Path.Combine(Path.GetTempPath(), $"{Guid.NewGuid()}.json");
+		try
+		{
+			string text = RunWithConsole(new Export(), $"{outputFile}\n");
+
+			Assert.Contains("Enter the output file path", text);
+			Assert.IsTrue(File.Exists(outputFile));
+			Assert.Contains("A dog on a beach.", File.ReadAllText(outputFile));
+		}
+		finally
+		{
+			File.Delete(outputFile);
+		}
+	}
+
+	[TestMethod]
+	public void ExportRunWithAnEmptyAnswerAbortsCleanly()
+	{
+		string text = RunWithConsole(new Export(), "\n");
+
+		Assert.Contains("No path provided. Aborting.", text);
+	}
+
+	[TestMethod]
+	public void SearchRunWithoutAQueryAsksForOne()
+	{
+		string text = RunWithConsole(new Search(), "dog\n");
+
+		Assert.Contains("Enter the search query", text);
+		Assert.Contains("Search results for \"dog\": 1 match(es)", text);
+	}
+
+	[TestMethod]
+	public void MenuItemsAskAgainOnEveryRun()
+	{
+		Action search = Menu.CreateVerbAction(typeof(Search));
+
+		string text = RunWithConsole(search, "dog\ncat\n");
+
+		Assert.Contains("Search results for \"dog\": 1 match(es)", text);
+		Assert.Contains("Search results for \"cat\": 0 match(es)", text);
+	}
+
+	private static string RunWithConsole(BaseVerb verb, string input) => RunWithConsole(verb.Run, input);
+
+	/// <summary>
+	/// Runs <paramref name="run"/> as many times as <paramref name="input"/> has lines, against a
+	/// database holding one description, with the console redirected.
+	/// </summary>
+	private static string RunWithConsole(Action run, string input)
+	{
+		PersistentState originalSettings = Program.Settings;
+		TextReader originalIn = Console.In;
+		TextWriter originalOut = Console.Out;
+		using StringReader reader = new(input);
+		using StringWriter output = new();
+		try
+		{
+			Program.Settings = new PersistentState();
+			Program.Settings.Descriptions[new string('a', 64)] = new ImageDescription
+			{
+				Hash = new string('a', 64),
+				SuggestedFileName = "dog-on-beach.jpg".As<FileName>(),
+				KnownPaths = [Path.Combine(Path.GetTempPath(), "a.jpg").As<AbsoluteFilePath>()],
+				Model = "llava".As<OllamaModelName>(),
+				DescribedAt = new DateTime(2026, 9, 27, 1, 7, 46, DateTimeKind.Utc),
+				FileSizeBytes = 1,
+				Description = "A dog on a beach.",
+			};
+			Console.SetIn(reader);
+			Console.SetOut(output);
+
+			int runs = input.Count(c => c == '\n');
+			for (int i = 0; i < runs; i++)
+			{
+				run();
+			}
+		}
+		finally
+		{
+			Console.SetIn(originalIn);
+			Console.SetOut(originalOut);
+			Program.Settings = originalSettings;
+		}
+
+		return output.ToString();
+	}
 }
diff --git a/ImageDescriber/Verbs/Export.cs b/ImageDescriber/Verbs/Export.cs
index f20a7e2..2d80f8d 100644
--- a/ImageDescriber/Verbs/Export.cs
+++ b/ImageDescriber/Verbs/Export.cs
@@ -29,6 +29,25 @@ internal sealed class Export : BaseVerb<Export>
 	[Option('o', "output", Required = true, HelpText = "Output file path (.json or .csv).")]
 	public string OutputPath { get; set; } = string.Empty;
 
+	internal override bool ValidateArgs()
+	{
+		// The menu runs verbs without CommandLineParser, which is what enforces Required = true
+		if (string.IsNullOrWhiteSpace(OutputPath))
+		{
+			Console.Write("Enter the output file path (.json or .csv): ");
+			string? input = Console.ReadLine()?.Trim();
+			if (string.IsNullOrEmpty(input))
+			{
+				Console.WriteLine("No path provided. Aborting.");
+				return false;
+			}
+
+			OutputPath = input;
+		}
+
+		return base.ValidateArgs();
+	}
+
 	internal override void Run(Export options)
 	{
 		Dictionary<string, ImageDescription> descriptions = Program.Settings.Descriptions;
diff --git a/ImageDescriber/Verbs/Menu.cs b/ImageDescriber/Verbs/Menu.cs
index 6330705..f9673d9 100644
--- a/ImageDescriber/Verbs/Menu.cs
+++ b/ImageDescriber/Verbs/Menu.cs
@@ -29,7 +29,7 @@ internal override void Run(Menu options)
 		}
 		else
 		{
-			RunPromptMenu(Console.In, Console.Out, [.. verbs.Select(verb => (GetMenuText(verb), (Action)(() => CreateVerb(verb).Execute())))]);
+			RunPromptMenu(Console.In, Console.Out, [.. verbs.Select(verb => (GetMenuText(verb), CreateVerbAction(verb)))]);
 		}
 	}
 
@@ -109,6 +109,12 @@ private sealed class ActionCommand(Action action) : ICommand
 		public void Execute() => action();
 	}
 
+	/// <summary>
+	/// Returns an action that runs a fresh instance of the verb each time, so a path or query
+	/// entered for one run is asked for again on the next rather than silently reused.
+	/// </summary>
+	internal static Action CreateVerbAction(Type verbType) => () => CreateVerb(verbType).Execute();
+
 	private static BaseVerb CreateVerb(Type verbType)
 	{
 		BaseVerb? verb = Activator.CreateInstance(verbType) as BaseVerb;
@@ -126,7 +132,7 @@ private static string GetMenuText(Type verbType)
 	private static LabelMenuItem CreateMenuItem(Type verbType) => new()
 	{
 		Text = GetMenuText(verbType),
-		Command = CreateVerb(verbType),
+		Command = new ActionCommand(CreateVerbAction(verbType)),
 		IsEnabled = true,
 	};
 }
diff --git a/ImageDescriber/Verbs/Search.cs b/ImageDescriber/Verbs/Search.cs
index 3a6c66c..8071cc2 100644
--- a/ImageDescriber/Verbs/Search.cs
+++ b/ImageDescriber/Verbs/Search.cs
@@ -15,6 +15,25 @@ internal sealed class Search : BaseVerb<Search>
 	[Option('q', "query", Required = true, HelpText = "The search query to find in descriptions.")]
 	public string Query { get; set; } = string.Empty;
 
+	internal override bool ValidateArgs()
+	{
+		// The menu runs verbs without CommandLineParser, which is what enforces Required = true
+		if (string.IsNullOrWhiteSpace(Query))
+		{
+			Console.Write("Enter the search query: ");
+			string? input = Console.ReadLine()?.Trim();
+			if (string.IsNullOrEmpty(input))
+			{
+				Console.WriteLine("No query provided. Aborting.");
+				return false;
+			}
+
+			Query = input;
+		}
+
+		return base.ValidateArgs();
+	}
+
 	internal override void Run(Search options)
 	{
 		if (string.IsNullOrWhiteSpace(options.Query))