diff --git a/private/util/validate_usr_symlinks.awk b/private/util/validate_usr_symlinks.awk
index a51ac9f03..23053a707 100644
--- a/private/util/validate_usr_symlinks.awk
+++ b/private/util/validate_usr_symlinks.awk
@@ -13,9 +13,9 @@ BEGIN {
 {
     original_path = $1
     path = original_path
-    # Normalize: strip leading ./ or /
-    sub(/^\.\//, "", path)
-    sub(/^\//, "", path)
+    # Normalize: strip any combination of leading ./ and /
+    # This ensures ./bin, /bin, bin, and even //bin are treated the same.
+    sub(/^(\.\/|\/)+/, "", path)
 
     if (path in expected) {
         if ($0 !~ /type=link/) {
diff --git a/private/util/validate_usr_symlinks_test.sh b/private/util/validate_usr_symlinks_test.sh
index 9d391a770..371f839f1 100755
--- a/private/util/validate_usr_symlinks_test.sh
+++ b/private/util/validate_usr_symlinks_test.sh
@@ -43,11 +43,20 @@ run "./lib64 type=link mode=0777 nlink=1 uid=0 gid=0 link=usr/lib64
 ./usr/bin/ls type=file mode=0755 nlink=1 uid=0 gid=0 size=12345" \
   || fail "content under ./usr/ alongside valid symlinks should pass"
 
+run "/home/user/bin type=dir mode=0755 nlink=2 uid=1000 gid=1000" \
+  || fail "deep paths containing 'bin' should pass"
+
 # --- failing cases ---
 
 run "./bin type=dir mode=0755 nlink=2 uid=0 gid=0" \
   && fail "./bin as a directory should fail" || true
 
+run "//bin type=dir mode=0755 nlink=2 uid=0 gid=0" \
+  && fail "//bin as a directory should fail" || true
+
+run "././bin type=dir mode=0755 nlink=2 uid=0 gid=0" \
+  && fail "././bin as a directory should fail" || true
+
 run "./bin type=link mode=0777 nlink=1 uid=0 gid=0 link=usr/sbin" \
   && fail "./bin -> usr/sbin should fail" || true
 
@@ -57,6 +66,12 @@ run "bin type=link mode=0777 nlink=1 uid=0 gid=0 link=usr/fin" \
 run "/bin type=link mode=0777 nlink=1 uid=0 gid=0 link=usr/fin" \
   && fail "/bin -> usr/fin should fail" || true
 
+run "//bin type=link mode=0777 nlink=1 uid=0 gid=0 link=usr/fin" \
+  && fail "//bin -> usr/fin should fail" || true
+
+run "././bin type=link mode=0777 nlink=1 uid=0 gid=0 link=usr/fin" \
+  && fail "././bin -> usr/fin should fail" || true
+
 run "./sbin type=link mode=0777 nlink=1 uid=0 gid=0 link=usr/bin" \
   && fail "./sbin -> usr/bin should fail (Debian keeps sbin separate)" || true