diff --git a/Sources/SWBUtil/FSProxy.swift b/Sources/SWBUtil/FSProxy.swift
index 943f3ab2..f222a63f 100644
--- a/Sources/SWBUtil/FSProxy.swift
+++ b/Sources/SWBUtil/FSProxy.swift
@@ -757,16 +757,15 @@ class LocalFS: FSProxy, @unchecked Sendable {
     }
 
     func realpath(_ path: Path) throws -> Path {
-        #if os(Windows)
-        guard exists(path) else {
+        if path.isAbsolute && !exists(path) {
             throw POSIXError(ENOENT, context: "realpath", path.str)
         }
-        return Path(path.str.standardizingPath)
-        #else
-        guard let result = SWBLibc.realpath(path.str, nil) else { throw POSIXError(errno, context: "realpath", path.str) }
-        defer { free(result) }
-        return Path(String(cString: result))
-        #endif
+        let url = URL(fileURLWithPath: path.str)
+        let values = try url.resolvingSymlinksInPath().resourceValues(forKeys: Set([URLResourceKey.canonicalPathKey]))
+        guard let canonicalPath = values.canonicalPath else {
+            throw POSIXError(ENOENT, context: "realpath", path.str)
+        }
+        return try Path(canonicalPath.canonicalPathRepresentation)
     }
 
     func isOnPotentiallyRemoteFileSystem(_ path: Path) -> Bool {
diff --git a/Sources/SWBUtil/Path.swift b/Sources/SWBUtil/Path.swift
index 28294f29..d9344286 100644
--- a/Sources/SWBUtil/Path.swift
+++ b/Sources/SWBUtil/Path.swift
@@ -927,6 +927,39 @@ extension Path {
     }
 }
 
+extension String {
+    @_spi(Testing) public var canonicalPathRepresentation: String {
+        get throws {
+            #if os(Windows)
+            return try withCString(encodedAs: UTF16.self) { platformPath in
+                return try platformPath.withCanonicalPathRepresentation { canonicalPath in
+                    return String(decodingCString: canonicalPath, as: UTF16.self)
+                }
+            }
+            #else
+            return self
+            #endif
+        }
+    }
+}
+
+extension Path {
+     @_spi(Testing) public var canonicalPathRepresentation: String {
+        get throws {
+            #if os(Windows)
+            return try withPlatformString { platformPath in
+                return try platformPath.withCanonicalPathRepresentation { canonicalPath in
+                    return String(decodingCString: canonicalPath, as: UTF16.self)
+                }
+            }
+            #else
+            return str
+            #endif
+        }
+    }
+}
+
+
 /// A wrapper for a string which is used to identify an absolute path on the file system.
 public struct AbsolutePath: Hashable, Equatable, Serializable, Sendable {
     public let path: Path
diff --git a/Tests/SWBUtilTests/FSProxyTests.swift b/Tests/SWBUtilTests/FSProxyTests.swift
index ebfced2a..67a09e64 100644
--- a/Tests/SWBUtilTests/FSProxyTests.swift
+++ b/Tests/SWBUtilTests/FSProxyTests.swift
@@ -17,6 +17,12 @@ import SWBLibc
 import SWBTestSupport
 @_spi(TestSupport) import SWBUtil
 
+#if canImport(System)
+public import System
+#else
+public import SystemPackage
+#endif
+
 @Suite fileprivate struct FSProxyTests {
 
 #if !os(Windows)
@@ -1333,6 +1339,41 @@ import SWBTestSupport
             #expect(try fs.read(dir.join("foo")) == ByteString(encodingAsUTF8: "a"))
         }
     }
+
+    @Test(.requireHostOS(.windows))
+    func realpathWindows() async throws {
+        let fs = localFS
+        let windir = try #require(getEnvironmentVariable("WINDIR"))
+        do {
+            // Case-insensitive comparison because WINDIR might be C:\WINDOWS while the actual path is C:\Windows
+            // The main thing is the \\?\ prefix handling
+            #expect(try fs.realpath(Path(windir)).str.caseInsensitiveCompare(windir) == .orderedSame)
+            #expect(try fs.realpath(Path(#"\\?\"# + windir)).str.caseInsensitiveCompare(windir) == .orderedSame)
+        }
+
+        do {
+            let root = Path(windir).drive
+            #expect(try fs.realpath(root.join("Program Files")).str.caseInsensitiveCompare(root.join("Program Files").str) == .orderedSame)
+
+            if !fs.exists(root.join("Progra~1")) {
+                withKnownIssue {
+                    Issue.record("8.3 filenames are likely disabled in this environment (running in a container?)")
+                }
+                return
+            }
+
+            #expect(try fs.realpath(root.join("Progra~1")).str.caseInsensitiveCompare(root.join("Program Files").str) == .orderedSame)
+            #expect(try fs.realpath(Path(#"\\?\"# + root.join("Progra~1").str)).str.caseInsensitiveCompare(root.join("Program Files").str) == .orderedSame)
+        }
+    }
+}
+
+fileprivate extension Path {
+    var drive: Path {
+        var fp = FilePath(str)
+        fp.components.removeAll()
+        return Path(fp.string).withTrailingSlash
+    }
 }
 
 /// Helper method to test file tree removal method on the given file system.
diff --git a/Tests/SWBUtilTests/PathWindowsTests.swift b/Tests/SWBUtilTests/PathWindowsTests.swift
index f81f7afb..8e7bf36b 100644
--- a/Tests/SWBUtilTests/PathWindowsTests.swift
+++ b/Tests/SWBUtilTests/PathWindowsTests.swift
@@ -12,7 +12,7 @@
 
 import Testing
 import SWBTestSupport
-import SWBUtil
+@_spi(Testing) import SWBUtil
 
 @Suite(.requireHostOS(.windows))
 fileprivate struct PathWindowsTests {
@@ -58,35 +58,3 @@ fileprivate struct PathWindowsTests {
         #expect(try Path(current.str.prefix(2) + String(repeating: "foo/bar/baz/", count: 22)).canonicalPathRepresentation == "\\\\?\\" + current.join(String(repeating: "\\foo\\bar\\baz", count: 22)).str)
     }
 }
-
-fileprivate extension String {
-    var canonicalPathRepresentation: String {
-        get throws {
-            #if os(Windows)
-            return try withCString(encodedAs: UTF16.self) { platformPath in
-                return try platformPath.withCanonicalPathRepresentation { canonicalPath in
-                    return String(decodingCString: canonicalPath, as: UTF16.self)
-                }
-            }
-            #else
-            return self
-            #endif
-        }
-    }
-}
-
-fileprivate extension Path {
-    var canonicalPathRepresentation: String {
-        get throws {
-            #if os(Windows)
-            return try withPlatformString { platformPath in
-                return try platformPath.withCanonicalPathRepresentation { canonicalPath in
-                    return String(decodingCString: canonicalPath, as: UTF16.self)
-                }
-            }
-            #else
-            return str
-            #endif
-        }
-    }
-}