diff --git a/tinyurl/src/main/resources/db/migration/V2__strip_short_code_leading_zeros.sql b/tinyurl/src/main/resources/db/migration/V2__strip_short_code_leading_zeros.sql
index 7e0d8d0..ce76e56 100644
--- a/tinyurl/src/main/resources/db/migration/V2__strip_short_code_leading_zeros.sql
+++ b/tinyurl/src/main/resources/db/migration/V2__strip_short_code_leading_zeros.sql
@@ -1,6 +1,10 @@
 -- Remove leading zeros from existing short codes, relax the minimum length constraint,
 -- and add creator tracking columns.
 
+-- Drop the old constraint first (required min 4 chars) so the UPDATE below can produce shorter codes
+ALTER TABLE url_mappings
+    DROP CONSTRAINT chk_short_code_format;
+
 -- Strip leading zeros from all existing short codes
 UPDATE url_mappings
 SET short_code = LTRIM(short_code, '0')
@@ -8,7 +12,6 @@ WHERE short_code ~ '^0+.+$';
 
 -- Update the format constraint to allow codes as short as 1 character
 ALTER TABLE url_mappings
-    DROP CONSTRAINT chk_short_code_format,
     ADD CONSTRAINT chk_short_code_format CHECK (short_code ~ '^[0-9a-zA-Z_-]{1,32}$');
 
 -- Add creator tracking columns