diff --git a/Source/Testably.Abstractions.Testing/Helpers/PathHelper.cs b/Source/Testably.Abstractions.Testing/Helpers/PathHelper.cs
index dddd3272f..a61cb86c5 100644
--- a/Source/Testably.Abstractions.Testing/Helpers/PathHelper.cs
+++ b/Source/Testably.Abstractions.Testing/Helpers/PathHelper.cs
@@ -1,6 +1,5 @@
 using System;
 using System.Diagnostics.CodeAnalysis;
-using System.IO;
 
 namespace Testably.Abstractions.Testing.Helpers;
 
@@ -161,9 +160,7 @@ private static void CheckPathCharacters(string path, MockFileSystem fileSystem,
 				fileSystem.Execute.Path.GetFullPath(path), hResult);
 		}
 
-		fileSystem.Execute.OnWindowsIf(path.LastIndexOf(':') > 1 &&
-		                               path.LastIndexOf(':') <
-		                               path.IndexOf(Path.DirectorySeparatorChar),
+		fileSystem.Execute.OnWindowsIf(path.LastIndexOf(':') > 1,
 			() => throw ExceptionFactory.PathHasIncorrectSyntax(
 				fileSystem.Execute.Path.GetFullPath(path), hResult));
 	}
diff --git a/Tests/Testably.Abstractions.Tests/FileSystem/File/CopyTests.cs b/Tests/Testably.Abstractions.Tests/FileSystem/File/CopyTests.cs
index 53de0c2e8..a43b5ecf1 100644
--- a/Tests/Testably.Abstractions.Tests/FileSystem/File/CopyTests.cs
+++ b/Tests/Testably.Abstractions.Tests/FileSystem/File/CopyTests.cs
@@ -107,7 +107,10 @@ public void
 		}
 		else
 		{
-			exception.Should().BeException<IOException>(hResult: -2147024773);
+			exception.Should().BeException<IOException>(
+				messageContains:
+				"The filename, directory name, or volume label syntax is incorrect",
+				hResult: -2147024773);
 		}
 	}
 
@@ -313,6 +316,27 @@ public void Copy_SourceAccessedWithWriteShare_ShouldNotThrowOnLinuxOrMac(
 		FileSystem.File.ReadAllText(destinationPath).Should().Be(sourceContents);
 	}
 
+	[SkippableTheory]
+	[AutoData]
+	public void Copy_SourceDirectoryMissing_ShouldThrowDirectoryNotFoundException(
+		string missingDirectory,
+		string sourceName,
+		string destinationName)
+	{
+		string source = FileSystem.Path.Combine(missingDirectory, sourceName);
+		Exception? exception = Record.Exception(() =>
+		{
+			FileSystem.File.Copy(source, destinationName);
+		});
+
+		exception.Should().BeException<DirectoryNotFoundException>(
+			messageContains: Test.IsNetFramework
+				? null
+				: $"'{FileSystem.Path.GetFullPath(source)}'",
+			hResult: -2147024893);
+		FileSystem.Should().NotHaveFile(destinationName);
+	}
+
 	[SkippableTheory]
 	[AutoData]
 	public void Copy_SourceIsDirectory_ShouldThrowUnauthorizedAccessException_AndNotCopyFile(
@@ -327,10 +351,10 @@ public void Copy_SourceIsDirectory_ShouldThrowUnauthorizedAccessException_AndNot
 		});
 
 		exception.Should().BeException<UnauthorizedAccessException>(
-			hResult: -2147024891,
 			messageContains: Test.IsNetFramework
 				? $"'{sourceName}'"
-				: $"'{FileSystem.Path.GetFullPath(sourceName)}'");
+				: $"'{FileSystem.Path.GetFullPath(sourceName)}'",
+			hResult: -2147024891);
 		FileSystem.Should().HaveDirectory(sourceName);
 		FileSystem.Should().NotHaveFile(destinationName);
 	}
@@ -379,10 +403,10 @@ public void Copy_SourceMissing_ShouldThrowFileNotFoundException(
 		});
 
 		exception.Should().BeException<FileNotFoundException>(
-			hResult: -2147024894,
 			messageContains: Test.IsNetFramework
 				? null
-				: $"'{FileSystem.Path.GetFullPath(sourceName)}'");
+				: $"'{FileSystem.Path.GetFullPath(sourceName)}'",
+			hResult: -2147024894);
 		FileSystem.Should().NotHaveFile(destinationName);
 	}
 }