diff --git a/src/DiffEngine.Tests/ToolOrderDuplicateTests.cs b/src/DiffEngine.Tests/ToolOrderDuplicateTests.cs
new file mode 100644
index 00000000..5410db3b
--- /dev/null
+++ b/src/DiffEngine.Tests/ToolOrderDuplicateTests.cs
@@ -0,0 +1,57 @@
+/// <summary>
+/// A repeated name in DiffEngine_ToolOrder.
+/// <para>
+/// Sort looked each requested tool up in Definitions, which holds every tool whether it is
+/// installed or not - so the lookup only ever failed on a second occurrence, because the first had
+/// removed it from the list. That was then reported as "is not installed", which was untrue, and
+/// since DiffTools resolves the order in a static constructor it was also permanent: every later
+/// use of DiffTools in that process threw TypeInitializationException.
+/// </para>
+/// </summary>
+[NotInParallel]
+public class ToolOrderDuplicateTests :
+    IDisposable
+{
+    [Test]
+    public async Task ARepeatedToolIsNotAnUninstalledOne()
+    {
+        // An installed one, chosen from what this machine actually has, since throwForNoTool is
+        // the flag under test and naming an absent tool would throw for the right reason
+        var installed = DiffTools.Resolved.FirstOrDefault(_ => _.Tool != null)?.Tool;
+        if (installed == null)
+        {
+            // No built in tool resolved here, so there is nothing to repeat
+            return;
+        }
+
+        DiffTools.UseOrder(true, installed.Value, installed.Value);
+
+        // Still ordered, rather than dropped along with the duplicate
+        await Assert.That(DiffTools.Resolved.Any(_ => _.Tool == installed)).IsTrue();
+    }
+
+    /// <summary>
+    /// And the flag still means what it says for a tool that genuinely is not here.
+    /// </summary>
+    [Test]
+    public async Task AnUninstalledToolStillThrows()
+    {
+        var installed = DiffTools.Resolved
+            .Where(_ => _.Tool != null)
+            .Select(_ => _.Tool!.Value)
+            .ToHashSet();
+
+        var absent = Enum.GetValues<DiffTool>().FirstOrDefault(_ => !installed.Contains(_));
+        if (installed.Count == Enum.GetValues<DiffTool>().Length)
+        {
+            // Every tool installed, which no real machine is
+            return;
+        }
+
+        await Assert.That(() => DiffTools.UseOrder(true, absent))
+            .Throws<Exception>();
+    }
+
+    public void Dispose() =>
+        DiffTools.Reset();
+}
diff --git a/src/DiffEngine/DiffTools_Add.cs b/src/DiffEngine/DiffTools_Add.cs
index 9b9af4db..2ca26ac6 100644
--- a/src/DiffEngine/DiffTools_Add.cs
+++ b/src/DiffEngine/DiffTools_Add.cs
@@ -118,10 +118,10 @@ static void InitTools(bool throwForNoTool, IEnumerable<DiffTool> order)
         firstTextTool = null;
         resolved.Clear();
 
-        foreach (var definition in ToolsOrder.Sort(throwForNoTool, order).Reverse())
+        foreach (var (definition, requested) in ToolsOrder.Sort(order).Reverse())
         {
             var tool = definition.Tool;
-            AddTool(
+            var added = AddTool(
                 tool.ToString(),
                 tool,
                 definition.AutoRefresh,
@@ -133,6 +133,16 @@ static void InitTools(bool throwForNoTool, IEnumerable<DiffTool> order)
                 definition.UseShellExecute,
                 definition.CreateNoWindow,
                 definition.KillLockingProcess);
+
+            // Here rather than in Sort, because this is where being installed is decided: Sort
+            // works from Definitions, which holds every tool whether it is on the machine or not,
+            // so it could never answer this question
+            if (added == null &&
+                requested &&
+                throwForNoTool)
+            {
+                throw new($"`DiffEngine_ToolOrder` is configured to use '{tool}' but it is not installed.");
+            }
         }
 
         custom.Reverse();
diff --git a/src/DiffEngine/ToolsOrder.cs b/src/DiffEngine/ToolsOrder.cs
index 2bac6e42..58904c02 100644
--- a/src/DiffEngine/ToolsOrder.cs
+++ b/src/DiffEngine/ToolsOrder.cs
@@ -1,28 +1,33 @@
 static class ToolsOrder
 {
-    public static IEnumerable<Definition> Sort(bool throwForNoTool, IEnumerable<DiffTool> order)
+    /// <summary>
+    /// The requested tools first, in the order asked for, then everything else. Each is flagged
+    /// with whether it was asked for, so the caller can tell a tool the user named and could not
+    /// have from one that simply is not installed on this machine and was never mentioned.
+    /// </summary>
+    public static IEnumerable<(Definition Definition, bool Requested)> Sort(IEnumerable<DiffTool> order)
     {
         var allTools = Definitions.Tools.ToList();
-        foreach (var diffTool in order)
+        // Distinct, because a repeated name is a typo rather than a request for two of something.
+        // Without it the second occurrence found nothing - the first had already removed it - and
+        // that was reported as "is not installed", which was both untrue and, from a static
+        // constructor, permanent: DiffEngine_ToolOrder=VisualStudio,VisualStudio turned every
+        // later use of DiffTools into a TypeInitializationException
+        foreach (var diffTool in order.Distinct())
         {
             var definition = allTools.SingleOrDefault(_ => _.Tool == diffTool);
             if (definition == null)
             {
-                if (!throwForNoTool)
-                {
-                    continue;
-                }
-
-                throw new($"`DiffEngine_ToolOrder` is configured to use '{diffTool}' but it is not installed.");
+                continue;
             }
 
-            yield return definition;
+            yield return (definition, true);
             allTools.Remove(definition);
         }
 
         foreach (var definition in allTools)
         {
-            yield return definition;
+            yield return (definition, false);
         }
     }
-}
\ No newline at end of file
+}