From 16ad7a809dbfce2498d4dac3201023e19872ef41 Mon Sep 17 00:00:00 2001
From: 218broadway-svg <254509107+218broadway-svg@users.noreply.github.com>
Date: Fri, 8 May 2026 21:05:44 +1000
Subject: [PATCH] Fix AnyBlob content type column removal

---
 .../liquibase/incremental-liquibase.spec.ts   | 34 +++++++++++++++++++
 .../changelog/updated_entity.xml.ejs          |  4 +++
 2 files changed, 38 insertions(+)

diff --git a/generators/liquibase/incremental-liquibase.spec.ts b/generators/liquibase/incremental-liquibase.spec.ts
index dcc5a425d088..7de76d2ae159 100644
--- a/generators/liquibase/incremental-liquibase.spec.ts
+++ b/generators/liquibase/incremental-liquibase.spec.ts
@@ -559,6 +559,40 @@ entity Customer {
     });
   });
 
+  describe('when removing a blob field with content type', () => {
+    before(async () => {
+      await helpers.runJDL(`
+${jdlApplication}
+entity Customer {
+    name String
+    contract AnyBlob
+}
+`);
+
+      await helpers
+        .runJDLInApplication(
+          `
+${jdlApplication}
+entity Customer {
+    name String
+}
+`,
+        )
+        .withMockedSource({ except: exceptSourceMethods })
+        .withMockedJHipsterGenerators({ except: exceptMockedGenerators })
+        .withOptions({
+          creationTimestamp: '2020-01-02',
+        });
+    });
+
+    it('should drop the blob field content type column', () => {
+      const updatedChangelog = `${SERVER_MAIN_RES_DIR}config/liquibase/changelog/20200102000100_updated_entity_Customer.xml`;
+
+      runResult.assertFileContent(updatedChangelog, 'column name="contract"');
+      runResult.assertFileContent(updatedChangelog, 'column name="contract_content_type"');
+    });
+  });
+
   describe('when adding a relationship', () => {
     before(async () => {
       await helpers
diff --git a/generators/liquibase/templates/src/main/resources/config/liquibase/changelog/updated_entity.xml.ejs b/generators/liquibase/templates/src/main/resources/config/liquibase/changelog/updated_entity.xml.ejs
index b54c9b153ae1..8798e8344cab 100644
--- a/generators/liquibase/templates/src/main/resources/config/liquibase/changelog/updated_entity.xml.ejs
+++ b/generators/liquibase/templates/src/main/resources/config/liquibase/changelog/updated_entity.xml.ejs
@@ -50,6 +50,10 @@
         <dropColumn tableName="<%- entity.entityTableName %>">
   <%_ for (field of removedFields) { _%>
             <column name="<%- field.columnName %>"/>
+    <%_ if (field.shouldCreateContentType) { _%>
+            <column name="<%- field.columnName %>_content_type"/>
+  <%_ }
+    _%>
   <%_ } _%>
         </dropColumn>
     </changeSet>