diff --git a/internal/common/service/common.document.service.go b/internal/common/service/common.document.service.go
index 44f2c116..a57aaa85 100644
--- a/internal/common/service/common.document.service.go
+++ b/internal/common/service/common.document.service.go
@@ -363,13 +363,19 @@ func (s *documentService) generateObjectKey(ext string) (string, error) {
 	}
 
 	u := uuid.New().String()
-	key := fmt.Sprintf("%s/%s%s", strings.Trim(s.keyPrefix, "/"), u, normalizedExt)
-	if s.keyPrefix == "" {
-		key = fmt.Sprintf("%s%s", u, normalizedExt)
+	keyPrefix := strings.Trim(s.keyPrefix, "/")
+	key := fmt.Sprintf("%s%s", u, normalizedExt)
+	if keyPrefix != "" {
+		key = fmt.Sprintf("%s/%s%s", keyPrefix, u, normalizedExt)
 	}
 
 	if len(key) > s.maxPathLength {
-		key = fmt.Sprintf("%s%s", u, normalizedExt)
+		compact := strings.ReplaceAll(u, "-", "")
+		if keyPrefix != "" {
+			key = fmt.Sprintf("%s/%s%s", keyPrefix, compact, normalizedExt)
+		} else {
+			key = fmt.Sprintf("%s%s", compact, normalizedExt)
+		}
 	}
 
 	if len(key) > s.maxPathLength {
diff --git a/internal/database/migrations/20260128035908_alter_documents_path_length.down.sql b/internal/database/migrations/20260128035908_alter_documents_path_length.down.sql
new file mode 100644
index 00000000..70a1e119
--- /dev/null
+++ b/internal/database/migrations/20260128035908_alter_documents_path_length.down.sql
@@ -0,0 +1,7 @@
+BEGIN;
+
+-- Migration: revert documents.path length
+ALTER TABLE documents
+    ALTER COLUMN path TYPE VARCHAR(50);
+
+COMMIT;
diff --git a/internal/database/migrations/20260128035908_alter_documents_path_length.up.sql b/internal/database/migrations/20260128035908_alter_documents_path_length.up.sql
new file mode 100644
index 00000000..80ed2c06
--- /dev/null
+++ b/internal/database/migrations/20260128035908_alter_documents_path_length.up.sql
@@ -0,0 +1,7 @@
+BEGIN;
+
+-- Migration: extend documents.path length for environment prefixes
+ALTER TABLE documents
+    ALTER COLUMN path TYPE VARCHAR(255);
+
+COMMIT;
diff --git a/internal/entities/document.go b/internal/entities/document.go
index 54974a02..a13dee0b 100644
--- a/internal/entities/document.go
+++ b/internal/entities/document.go
@@ -7,7 +7,7 @@ type Document struct {
 	DocumentableType string    `gorm:"size:50;not null;index:documents_documentable_polymorphic,priority:1"`
 	DocumentableId   uint64    `gorm:"not null;index:documents_documentable_polymorphic,priority:2"`
 	Type             string    `gorm:"size:50;not null"`
-	Path             string    `gorm:"size:50;not null"`
+	Path             string    `gorm:"size:255;not null"`
 	Name             string    `gorm:"size:50;not null"`
 	Ext              string    `gorm:"size:50;not null"`
 	Size             float64   `gorm:"type:numeric(15,3);not null"`