diff --git a/src/PrettyPrompt/Panes/CodePane.cs b/src/PrettyPrompt/Panes/CodePane.cs
index 0f5ba53..fec99bb 100644
--- a/src/PrettyPrompt/Panes/CodePane.cs
+++ b/src/PrettyPrompt/Panes/CodePane.cs
@@ -4,18 +4,13 @@
 // file, You can obtain one at https://mozilla.org/MPL/2.0/.
 #endregion
 
-using System;
-using System.Collections.Generic;
 using System.Diagnostics;
-using System.Linq;
-using System.Text;
 using System.Threading;
 using System.Threading.Tasks;
 using PrettyPrompt.Consoles;
 using PrettyPrompt.Documents;
 using PrettyPrompt.Rendering;
 using PrettyPrompt.TextSelection;
-using TextCopy;
 using static System.ConsoleKey;
 using static System.ConsoleModifiers;
 
@@ -26,7 +21,7 @@ internal class CodePane : IKeyPressHandler
     private readonly IConsole console;
     private readonly PromptConfiguration configuration;
     private readonly IPromptCallbacks promptCallbacks;
-    private readonly IClipboard clipboard;
+    private readonly WrappedClipboard clipboard;
     private readonly SelectionKeyPressHandler selectionHandler;
     private int topCoordinate;
     private int codeAreaWidth;
@@ -115,7 +110,7 @@ public int EmptySpaceAtBottomOfWindowHeight
         }
     }
 
-    public CodePane(IConsole console, PromptConfiguration configuration, IPromptCallbacks promptCallbacks, IClipboard clipboard)
+    public CodePane(IConsole console, PromptConfiguration configuration, IPromptCallbacks promptCallbacks, WrappedClipboard clipboard)
     {
         this.console = console;
         this.configuration = configuration;
@@ -267,9 +262,11 @@ public async Task OnKeyDown(KeyPress key, CancellationToken cancellationToken)
             case (Control, X) when selection.TryGet(out var selectionValue):
                 {
                     var cutContent = Document.GetText(selectionValue).ToString();
-                    Selection = null;
-                    Document.Remove(this, selectionValue);
-                    await clipboard.SetTextAsync(cutContent, cancellationToken).ConfigureAwait(false);
+                    if (await clipboard.TrySetTextAsync(cutContent, cancellationToken).ConfigureAwait(false))
+                    {
+                        Selection = null;
+                        Document.Remove(this, selectionValue);
+                    }
                     break;
                 }
             case (Control, X) or (Shift, Delete):
@@ -285,10 +282,16 @@ public async Task OnKeyDown(KeyPress key, CancellationToken cancellationToken)
 
                     if (key.ObjectPattern is (Control, X))
                     {
-                        await clipboard.SetTextAsync(Document.GetText(span).ToString(), cancellationToken).ConfigureAwait(false);
+                        if (await clipboard.TrySetTextAsync(Document.GetText(span).ToString(), cancellationToken).ConfigureAwait(false))
+                        {
+                            Document.Remove(this, span);
+                        }
+                    }
+                    else
+                    {
+                        // Shift+Delete just deletes the line; it never touches the clipboard.
+                        Document.Remove(this, span);
                     }
-
-                    Document.Remove(this, span);
                     break;
                 }
             case (Control, K) when selection is null: // Ctrl+K = delete from caret to end of the current line (emacs/readline kill-line); deletes only, does not write the clipboard
@@ -308,19 +311,23 @@ public async Task OnKeyDown(KeyPress key, CancellationToken cancellationToken)
             case (Control, C) when selection.TryGet(out var selectionValue):
                 {
                     var copiedContent = Document.GetText(selectionValue).ToString();
-                    await clipboard.SetTextAsync(copiedContent, cancellationToken).ConfigureAwait(false);
+                    // copy doesn't mutate the document, so a failed clipboard write is simply a no-op
+                    _ = await clipboard.TrySetTextAsync(copiedContent, cancellationToken).ConfigureAwait(false);
                     break;
                 }
             case (Control | Shift, C):
-                await clipboard.SetTextAsync(Document.GetText(), cancellationToken).ConfigureAwait(false);
+                _ = await clipboard.TrySetTextAsync(Document.GetText(), cancellationToken).ConfigureAwait(false);
                 break;
             case (Shift, Insert) when key.PastedText is not null:
                 PasteText(key.PastedText);
                 break;
             case (Control, V) or (Control | Shift, V) or (Shift, Insert):
                 {
-                    var clipboardText = await clipboard.GetTextAsync(cancellationToken).ConfigureAwait(false);
-                    PasteText(clipboardText);
+                    var (success, clipboardText) = await clipboard.TryGetTextAsync(cancellationToken).ConfigureAwait(false);
+                    if (success)
+                    {
+                        PasteText(clipboardText);
+                    }
                     break;
                 }
             case (Control, Z):
@@ -395,8 +402,7 @@ string DedentMultipleLinesAndFilter(string text)
                 else
                 {
                     var leadingIndent = nonEmptyLines
-                        .Select(line => line.TakeWhile(char.IsWhiteSpace).Count())
-                        .Min();
+                        .Min(line => line.TakeWhile(char.IsWhiteSpace).Count());
 
                     if (leadingIndent == 0)
                     {
diff --git a/src/PrettyPrompt/Prompt.cs b/src/PrettyPrompt/Prompt.cs
index 3637ce2..cc13119 100644
--- a/src/PrettyPrompt/Prompt.cs
+++ b/src/PrettyPrompt/Prompt.cs
@@ -16,7 +16,6 @@
 using PrettyPrompt.Panes;
 using PrettyPrompt.Rendering;
 using PrettyPrompt.TextSelection;
-using TextCopy;
 
 namespace PrettyPrompt;
 
@@ -27,7 +26,7 @@ public sealed class Prompt : IPrompt, IAsyncDisposable
     private readonly HistoryLog history;
     private readonly PromptConfiguration configuration;
     private readonly CancellationManager cancellationManager;
-    private readonly IClipboard clipboard;
+    private readonly WrappedClipboard clipboard;
     private readonly SyntaxHighlighter highlighter;
     private readonly IPromptCallbacks promptCallbacks;
     private Task? savePersistentHistoryTask;
@@ -51,7 +50,7 @@ public Prompt(
         this.configuration = configuration ?? new PromptConfiguration();
         this.history = new HistoryLog(persistentHistoryFilepath, this.configuration.KeyBindings);
         this.cancellationManager = new CancellationManager(this.console);
-        this.clipboard = (console is IConsoleWithClipboard consoleWithClipboard) ? consoleWithClipboard.Clipboard : new WrappedClipboard();
+        this.clipboard = (console is IConsoleWithClipboard consoleWithClipboard) ? new WrappedClipboard(consoleWithClipboard.Clipboard) : new WrappedClipboard();
 
         promptCallbacks = callbacks ?? new PromptCallbacks();
         this.highlighter = new SyntaxHighlighter(promptCallbacks, PromptConfiguration.HasUserOptedOutFromColor);
diff --git a/src/PrettyPrompt/TextSelection/WrappedClipboard.cs b/src/PrettyPrompt/TextSelection/WrappedClipboard.cs
index ceb9746..3397cf4 100644
--- a/src/PrettyPrompt/TextSelection/WrappedClipboard.cs
+++ b/src/PrettyPrompt/TextSelection/WrappedClipboard.cs
@@ -4,62 +4,117 @@
 using TextCopy;
 
 namespace PrettyPrompt.TextSelection;
-internal class WrappedClipboard : IClipboard
+
+/// <summary>
+/// Wraps the <see cref="TextCopy"/> clipboard so that transient clipboard failures never crash the prompt.
+/// The OS clipboard can be flaky for reasons outside our control - e.g. no X display available, or the
+/// underlying helper process timing out (TextCopy shells out with a hard-coded 500ms timeout on Linux).
+/// A cut/copy/paste hiccup like that should degrade gracefully rather than abort the whole prompt, so the
+/// Try* methods report failure instead of throwing. Callers can then avoid destructive edits - e.g. not
+/// removing cut text that never made it to the clipboard.
+///
+/// A missing clipboard executable (xsel/clip.exe) is different: it's an actionable setup problem rather
+/// than a transient hiccup, so the Try* methods surface it as an exception with a helpful message instead
+/// of silently swallowing it.
+/// </summary>
+internal sealed class WrappedClipboard
 {
     private const string MissingExecutableError = "Could not execute process";
     private const string HelpfulErrorMessage = "Could not access clipboard. Check that xsel (Linux) or clip.exe (WSL) is installed.";
-    private readonly Clipboard clipboard;
+
+    private readonly IClipboard clipboard;
 
     public WrappedClipboard()
+        : this(new Clipboard())
+    {
+    }
+
+    public WrappedClipboard(IClipboard clipboard)
     {
-        this.clipboard = new Clipboard();
+        this.clipboard = clipboard;
     }
 
-    public string? GetText()
+    /// <summary>Reads the clipboard. Returns <see langword="false"/> (with <paramref name="text"/> null) if the read failed.</summary>
+    public bool TryGetText(out string? text)
     {
         try
         {
-            return clipboard.GetText();
+            text = clipboard.GetText();
+            return true;
         }
-        catch (Exception ex) when (ex.Message.Contains(MissingExecutableError))
+        catch (Exception ex) when (IsMissingExecutable(ex))
         {
             throw new Exception(HelpfulErrorMessage, ex);
         }
+        catch
+        {
+            text = null;
+            return false;
+        }
     }
 
-    public async Task<string?> GetTextAsync(CancellationToken cancellation = default)
+    /// <summary>Reads the clipboard. <c>Success</c> is <see langword="false"/> (and <c>Text</c> null) if the read failed.</summary>
+    public async Task<(bool Success, string? Text)> TryGetTextAsync(CancellationToken cancellation = default)
     {
         try
         {
-            return await clipboard.GetTextAsync(cancellation).ConfigureAwait(false);
+            return (true, await clipboard.GetTextAsync(cancellation).ConfigureAwait(false));
+        }
+        catch (OperationCanceledException) when (cancellation.IsCancellationRequested)
+        {
+            throw;
         }
-        catch (Exception ex) when (ex.Message.Contains(MissingExecutableError))
+        catch (Exception ex) when (IsMissingExecutable(ex))
         {
             throw new Exception(HelpfulErrorMessage, ex);
         }
+        catch
+        {
+            return (false, null);
+        }
     }
 
-    public void SetText(string text)
+    /// <summary>Writes to the clipboard. Returns <see langword="false"/> if the write failed.</summary>
+    public bool TrySetText(string text)
     {
         try
         {
             clipboard.SetText(text);
+            return true;
         }
-        catch (Exception ex) when (ex.Message.Contains(MissingExecutableError))
+        catch (Exception ex) when (IsMissingExecutable(ex))
         {
             throw new Exception(HelpfulErrorMessage, ex);
         }
+        catch
+        {
+            return false;
+        }
     }
 
-    public async Task SetTextAsync(string text, CancellationToken cancellation = default)
+    /// <summary>Writes to the clipboard. Returns <see langword="false"/> if the write failed.</summary>
+    public async Task<bool> TrySetTextAsync(string text, CancellationToken cancellation = default)
     {
         try
         {
             await clipboard.SetTextAsync(text, cancellation).ConfigureAwait(false);
+            return true;
         }
-        catch (Exception ex) when (ex.Message.Contains(MissingExecutableError))
+        catch (OperationCanceledException) when (cancellation.IsCancellationRequested)
+        {
+            throw;
+        }
+        catch (Exception ex) when (IsMissingExecutable(ex))
         {
             throw new Exception(HelpfulErrorMessage, ex);
         }
+        catch
+        {
+            return false;
+        }
     }
+
+    // A missing clipboard executable is reported by TextCopy as a "Could not execute process" error;
+    // unlike a timeout, reinstalling the tool is the fix, so we surface it rather than swallow it.
+    private static bool IsMissingExecutable(Exception ex) => ex.Message.Contains(MissingExecutableError);
 }
diff --git a/tests/PrettyPrompt.Tests/ClipboardTests.cs b/tests/PrettyPrompt.Tests/ClipboardTests.cs
index 902a90a..23dc832 100644
--- a/tests/PrettyPrompt.Tests/ClipboardTests.cs
+++ b/tests/PrettyPrompt.Tests/ClipboardTests.cs
@@ -3,6 +3,7 @@
 using System.Collections.Generic;
 using System.Linq;
 using System.Text;
+using System.Threading;
 using System.Threading.Tasks;
 using Xunit;
 
@@ -29,16 +30,61 @@ public async Task Clipboard_WrappedCopyPasting()
         var console = ConsoleStub.NewConsole();
         using (console.ProtectClipboard())
         {
-            clipboard.SetText("hello");
+            Assert.True(clipboard.TrySetText("hello"));
             await Task.Delay(100, TestContext.Current.CancellationToken);
-            var pasted = clipboard.GetText();
+            Assert.True(clipboard.TryGetText(out var pasted));
             Assert.Equal("hello", pasted);
 
-            await clipboard.SetTextAsync("world", TestContext.Current.CancellationToken);
+            Assert.True(await clipboard.TrySetTextAsync("world", TestContext.Current.CancellationToken));
             await Task.Delay(100, TestContext.Current.CancellationToken);
-            pasted = await clipboard.GetTextAsync(TestContext.Current.CancellationToken);
-            Assert.Equal("world", pasted);
+            var (success, pastedAsync) = await clipboard.TryGetTextAsync(TestContext.Current.CancellationToken);
+            Assert.True(success);
+            Assert.Equal("world", pastedAsync);
         }
     }
 
+    [Fact]
+    public async Task Clipboard_WhenUnderlyingClipboardThrows_ReportsFailureWithoutThrowing()
+    {
+        // The OS clipboard can fail for reasons outside our control (missing xsel/clip.exe, no display,
+        // the TextCopy helper process timing out - see https://github.com/waf/CSharpRepl/issues/327).
+        // None of those should propagate out and crash the prompt; the Try* methods report failure instead,
+        // which lets callers avoid destructive edits (e.g. not removing cut text that was never copied).
+        var throwingClipboard = new WrappedClipboard(new ThrowingClipboard());
+
+        Assert.False(throwingClipboard.TryGetText(out var text));
+        Assert.Null(text);
+
+        var (success, asyncText) = await throwingClipboard.TryGetTextAsync(TestContext.Current.CancellationToken);
+        Assert.False(success);
+        Assert.Null(asyncText);
+
+        Assert.False(throwingClipboard.TrySetText("hello"));
+        Assert.False(await throwingClipboard.TrySetTextAsync("hello", TestContext.Current.CancellationToken));
+    }
+
+    [Fact]
+    public async Task Clipboard_WhenExecutableMissing_ThrowsHelpfulError()
+    {
+        // A missing clipboard tool (xsel/clip.exe) is an actionable setup problem rather than a transient
+        // hiccup, so we surface it with a helpful message rather than silently swallowing it.
+        var clipboard = new WrappedClipboard(new ThrowingClipboard("Could not execute process"));
+
+        Assert.Contains("xsel", Assert.Throws<Exception>(() => clipboard.TryGetText(out _)).Message);
+        Assert.Contains("xsel", (await Assert.ThrowsAsync<Exception>(async () => await clipboard.TryGetTextAsync(TestContext.Current.CancellationToken))).Message);
+        Assert.Contains("xsel", Assert.Throws<Exception>(() => clipboard.TrySetText("hello")).Message);
+        Assert.Contains("xsel", (await Assert.ThrowsAsync<Exception>(() => clipboard.TrySetTextAsync("hello", TestContext.Current.CancellationToken))).Message);
+    }
+
+    [Fact]
+    public async Task Clipboard_WhenCancelled_PropagatesCancellation()
+    {
+        // Genuine cancellation should still surface - it isn't a clipboard failure to swallow.
+        var clipboard = new WrappedClipboard(new ThrowingClipboard());
+        using var cts = new CancellationTokenSource();
+        cts.Cancel();
+
+        await Assert.ThrowsAnyAsync<OperationCanceledException>(async () => await clipboard.TryGetTextAsync(cts.Token));
+        await Assert.ThrowsAnyAsync<OperationCanceledException>(() => clipboard.TrySetTextAsync("hello", cts.Token));
+    }
 }
diff --git a/tests/PrettyPrompt.Tests/ConsoleStub.cs b/tests/PrettyPrompt.Tests/ConsoleStub.cs
index 7cf5a84..07405d9 100644
--- a/tests/PrettyPrompt.Tests/ConsoleStub.cs
+++ b/tests/PrettyPrompt.Tests/ConsoleStub.cs
@@ -367,4 +367,36 @@ public abstract class ConsoleWithClipboard : IConsoleWithClipboard
     public void WriteError(StringBuilder value, bool hideCursor) => WriteError(value.ToString());
     public void WriteErrorLine(StringBuilder value, bool hideCursor) => WriteErrorLine(value.ToString());
     public void WriteLine(StringBuilder value, bool hideCursor) => WriteLine(value.ToString());
+}
+
+/// <summary>
+/// An <see cref="IClipboard"/> that always fails, used to simulate an unavailable or flaky OS clipboard.
+/// The default message mimics a transient failure (e.g. the TextCopy helper process timing out); pass a
+/// message containing "Could not execute process" to mimic a missing xsel/clip.exe executable.
+/// See https://github.com/waf/CSharpRepl/issues/327.
+/// </summary>
+internal sealed class ThrowingClipboard : IClipboard
+{
+    private readonly string message;
+
+    public ThrowingClipboard(string message = "Process timed out.")
+    {
+        this.message = message;
+    }
+
+    public string? GetText() => throw new Exception(message);
+
+    public Task<string?> GetTextAsync(CancellationToken cancellation = default)
+    {
+        cancellation.ThrowIfCancellationRequested();
+        throw new Exception(message);
+    }
+
+    public void SetText(string text) => throw new Exception(message);
+
+    public Task SetTextAsync(string text, CancellationToken cancellation = default)
+    {
+        cancellation.ThrowIfCancellationRequested();
+        throw new Exception(message);
+    }
 }
\ No newline at end of file
diff --git a/tests/PrettyPrompt.Tests/HistoryTests.cs b/tests/PrettyPrompt.Tests/HistoryTests.cs
index 6f0d069..e5b3319 100644
--- a/tests/PrettyPrompt.Tests/HistoryTests.cs
+++ b/tests/PrettyPrompt.Tests/HistoryTests.cs
@@ -8,6 +8,7 @@
 using PrettyPrompt.Consoles;
 using PrettyPrompt.History;
 using PrettyPrompt.Panes;
+using PrettyPrompt.TextSelection;
 using System;
 using System.IO;
 using System.Text;
@@ -485,7 +486,7 @@ public async Task History_InvalidBase64Value_DoesNotCrash()
             Substitute.For<IConsole>(),
             new PromptConfiguration(),
             Substitute.For<IPromptCallbacks>(),
-            Substitute.For<IClipboard>()
+            new WrappedClipboard(Substitute.For<IClipboard>())
         );
         history.Track(codePane);
 
diff --git a/tests/PrettyPrompt.Tests/RendererTests.cs b/tests/PrettyPrompt.Tests/RendererTests.cs
index 13b540b..532c646 100644
--- a/tests/PrettyPrompt.Tests/RendererTests.cs
+++ b/tests/PrettyPrompt.Tests/RendererTests.cs
@@ -5,6 +5,7 @@
 using NSubstitute;
 using PrettyPrompt.Consoles;
 using PrettyPrompt.Panes;
+using PrettyPrompt.TextSelection;
 using TextCopy;
 using Xunit;
 
@@ -98,7 +99,7 @@ public async Task RenderOutput_ConsoleHeightTooSmallAndCursorOnFirstLine_ShowsIn
     private (CodePane codePane, CompletionPane completionPane, OverloadPane overloadPane) BuildUIPanes(string typedInput)
     {
         var callbacks = Substitute.For<IPromptCallbacks>();
-        var codePane = new CodePane(console, configuration, new PromptCallbacks(), Substitute.For<IClipboard>());
+        var codePane = new CodePane(console, configuration, new PromptCallbacks(), new WrappedClipboard(Substitute.For<IClipboard>()));
         codePane.Document.InsertAtCaret(codePane, typedInput);
         var overloadPane = new OverloadPane(codePane, callbacks, configuration)
         {
diff --git a/tests/PrettyPrompt.Tests/SelectionTests.cs b/tests/PrettyPrompt.Tests/SelectionTests.cs
index 17971d6..e40f9be 100644
--- a/tests/PrettyPrompt.Tests/SelectionTests.cs
+++ b/tests/PrettyPrompt.Tests/SelectionTests.cs
@@ -8,6 +8,7 @@
 using System.Collections.Generic;
 using System.Linq;
 using System.Threading.Tasks;
+using NSubstitute;
 using Xunit;
 using static System.ConsoleKey;
 using static System.ConsoleModifiers;
@@ -162,6 +163,45 @@ public async Task ReadLine_CutText_CanBePasted()
         }
     }
 
+    [Fact]
+    public async Task ReadLine_CutOnEmptyPromptWithFailingClipboard_DoesNotCrash()
+    {
+        // Exact repro from https://github.com/waf/CSharpRepl/issues/327: pressing Ctrl+X on an (empty) prompt
+        // shells out to the OS clipboard, which can time out or otherwise fail. That must not crash the prompt.
+        var console = ConsoleStub.NewConsole();
+        console.Clipboard.Returns(new ThrowingClipboard());
+        using (console.ProtectClipboard())
+        {
+            console.StubInput($"{Control}{X}{Enter}");
+
+            var prompt = new Prompt(console: console);
+            var result = await prompt.ReadLineAsync();
+
+            Assert.True(result.IsSuccess);
+            Assert.Equal("", result.Text);
+        }
+    }
+
+    [Fact]
+    public async Task ReadLine_CutSelectionWithFailingClipboard_PreservesText()
+    {
+        // If the clipboard write fails, the cut must be a no-op rather than silently destroying the user's
+        // text - we only remove the selection once it's safely on the clipboard.
+        // https://github.com/waf/CSharpRepl/issues/327
+        var console = ConsoleStub.NewConsole();
+        console.Clipboard.Returns(new ThrowingClipboard());
+        using (console.ProtectClipboard())
+        {
+            console.StubInput($"hello world", $"{Shift}{Home}{Control}{X}{Enter}");
+
+            var prompt = new Prompt(console: console);
+            var result = await prompt.ReadLineAsync();
+
+            Assert.True(result.IsSuccess);
+            Assert.Equal("hello world", result.Text);
+        }
+    }
+
     [Fact]
     public async Task ReadLine_Delete_LeftSelection()
     {