diff --git a/internal/smartlink/smartlink.go b/internal/smartlink/smartlink.go
index f32c806a6b..c101abde5e 100644
--- a/internal/smartlink/smartlink.go
+++ b/internal/smartlink/smartlink.go
@@ -40,6 +40,8 @@ func LinkContents(src, dest string) error {
 // Link creates a link from src to target. MS decided to support Symlinks but only if you opt into developer mode (go figure),
 // which we cannot reasonably force on our users. So on Windows we will instead create dirs and hardlinks.
 func Link(src, dest string) error {
+	originalSrc := src
+
 	var err error
 	src, dest, err = resolvePaths(src, dest)
 	if err != nil {
@@ -47,11 +49,14 @@ func Link(src, dest string) error {
 	}
 
 	if fileutils.IsDir(src) {
-		if isSymlink(src) {
+		if fileutils.IsSymlink(originalSrc) {
+			// If the original src is a symlink, the resolved src is no longer a symlink and could point
+			// to a parent directory, resulting in a recursive directory structure.
+			// Avoid any potential problems by simply linking the original link to the target.
 			// Links to directories are okay on Linux and macOS, but will fail on Windows.
 			// If we ever get here on Windows, the artifact being deployed is bad and there's nothing we
 			// can do about it except receive the report from Rollbar and report it internally.
-			return linkFile(src, dest)
+			return linkFile(originalSrc, dest)
 		}
 
 		if err := fileutils.Mkdir(dest); err != nil {
@@ -138,20 +143,15 @@ func UnlinkContents(src, dest string) error {
 	return nil
 }
 
-func isSymlink(src string) bool {
-	target, err := fileutils.SymlinkTarget(src)
-	return err == nil && src != target
-}
-
 // resolvePaths will resolve src and dest to absolute paths and return them.
 // This is to ensure that we're always comparing apples to apples when doing string comparisons on paths.
 func resolvePaths(src, dest string) (string, string, error) {
 	var err error
-	src, err = filepath.Abs(filepath.Clean(src))
+	src, err = fileutils.ResolveUniquePath(src)
 	if err != nil {
 		return "", "", errs.Wrap(err, "Could not resolve src path")
 	}
-	dest, err = filepath.Abs(filepath.Clean(dest))
+	dest, err = fileutils.ResolveUniquePath(dest)
 	if err != nil {
 		return "", "", errs.Wrap(err, "Could not resolve dest path")
 	}