diff --git a/internal/diff/diff.go b/internal/diff/diff.go
index 080845b0..48f8b5e9 100644
--- a/internal/diff/diff.go
+++ b/internal/diff/diff.go
@@ -1603,14 +1603,14 @@ func (d *ddlDiff) generateCreateSQL(targetSchema string, collector *diffCollecto
 	// See https://github.com/pgplex/pgschema/issues/253
 	generateDropPrivilegesSQL(d.revokedDefaultGrantsOnNewTables, targetSchema, collector)
 
-	// Create explicit object privileges
-	generateCreatePrivilegesSQL(d.addedPrivileges, targetSchema, collector)
-
-	// Create column-level privileges
-	generateCreateColumnPrivilegesSQL(d.addedColumnPrivileges, targetSchema, collector)
-
 	// Revoke default PUBLIC privileges (new revokes)
 	generateRevokeDefaultPrivilegesSQL(d.addedRevokedDefaultPrivs, targetSchema, collector)
+
+	// Note: Explicit privilege creates and modifications are handled in generateModifySQL
+	// (after object modifications/recreations) to ensure:
+	// 1. DROP+CREATE'd objects (e.g., materialized views) don't wipe out privilege changes
+	// 2. REVOKEs from modifications execute before new GRANTs
+	// See https://github.com/pgplex/pgschema/issues/324
 }
 
 // generateModifySQL generates ALTER statements
@@ -1653,11 +1653,15 @@ func (d *ddlDiff) generateModifySQL(targetSchema string, collector *diffCollecto
 	// Modify default privileges
 	generateModifyDefaultPrivilegesSQL(d.modifiedDefaultPrivileges, targetSchema, collector)
 
-	// Modify explicit object privileges
+	// All explicit privilege operations run AFTER object modifications/recreations
+	// to avoid DROP+CREATE'd objects (e.g., materialized views) wiping out privilege changes.
+	// Modifications (which contain REVOKEs) run before creates (which contain GRANTs)
+	// to prevent table-level REVOKEs from undoing column-level GRANTs.
+	// See https://github.com/pgplex/pgschema/issues/324
 	generateModifyPrivilegesSQL(d.modifiedPrivileges, targetSchema, collector)
-
-	// Modify column-level privileges
 	generateModifyColumnPrivilegesSQL(d.modifiedColumnPrivileges, targetSchema, collector)
+	generateCreatePrivilegesSQL(d.addedPrivileges, targetSchema, collector)
+	generateCreateColumnPrivilegesSQL(d.addedColumnPrivileges, targetSchema, collector)
 }
 
 // generateDropSQL generates DROP statements in reverse dependency order
diff --git a/testdata/diff/privilege/issue_324_grant_revoke_order/diff.sql b/testdata/diff/privilege/issue_324_grant_revoke_order/diff.sql
new file mode 100644
index 00000000..83414f97
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_grant_revoke_order/diff.sql
@@ -0,0 +1,3 @@
+REVOKE UPDATE ON TABLE sometable FROM app_user;
+
+GRANT UPDATE (somecolumn) ON TABLE sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_grant_revoke_order/new.sql b/testdata/diff/privilege/issue_324_grant_revoke_order/new.sql
new file mode 100644
index 00000000..1c12601f
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_grant_revoke_order/new.sql
@@ -0,0 +1,10 @@
+DO $$
+BEGIN
+    IF NOT EXISTS (SELECT 1 FROM pg_roles WHERE rolname = 'app_user') THEN
+        CREATE ROLE app_user;
+    END IF;
+END $$;
+
+CREATE TABLE sometable (somecolumn text);
+
+GRANT UPDATE (somecolumn) ON sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_grant_revoke_order/old.sql b/testdata/diff/privilege/issue_324_grant_revoke_order/old.sql
new file mode 100644
index 00000000..72808b90
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_grant_revoke_order/old.sql
@@ -0,0 +1,10 @@
+DO $$
+BEGIN
+    IF NOT EXISTS (SELECT 1 FROM pg_roles WHERE rolname = 'app_user') THEN
+        CREATE ROLE app_user;
+    END IF;
+END $$;
+
+CREATE TABLE sometable (somecolumn text);
+
+GRANT UPDATE ON sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_grant_revoke_order/plan.json b/testdata/diff/privilege/issue_324_grant_revoke_order/plan.json
new file mode 100644
index 00000000..78de0b2d
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_grant_revoke_order/plan.json
@@ -0,0 +1,26 @@
+{
+  "version": "1.0.0",
+  "pgschema_version": "1.7.2",
+  "created_at": "1970-01-01T00:00:00Z",
+  "source_fingerprint": {
+    "hash": "2f50f8550c48f6ac58cde417097cdd7c293b3ae0d9bd8861b197edb73e80b148"
+  },
+  "groups": [
+    {
+      "steps": [
+        {
+          "sql": "REVOKE UPDATE ON TABLE sometable FROM app_user;",
+          "type": "privilege",
+          "operation": "drop",
+          "path": "privileges.TABLE.sometable.app_user"
+        },
+        {
+          "sql": "GRANT UPDATE (somecolumn) ON TABLE sometable TO app_user;",
+          "type": "column_privilege",
+          "operation": "create",
+          "path": "column_privileges.TABLE.sometable.somecolumn.app_user"
+        }
+      ]
+    }
+  ]
+}
diff --git a/testdata/diff/privilege/issue_324_grant_revoke_order/plan.sql b/testdata/diff/privilege/issue_324_grant_revoke_order/plan.sql
new file mode 100644
index 00000000..83414f97
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_grant_revoke_order/plan.sql
@@ -0,0 +1,3 @@
+REVOKE UPDATE ON TABLE sometable FROM app_user;
+
+GRANT UPDATE (somecolumn) ON TABLE sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_grant_revoke_order/plan.txt b/testdata/diff/privilege/issue_324_grant_revoke_order/plan.txt
new file mode 100644
index 00000000..7c3bd47f
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_grant_revoke_order/plan.txt
@@ -0,0 +1,18 @@
+Plan: 1 to add, 1 to drop.
+
+Summary by type:
+  privileges: 1 to drop
+  column privileges: 1 to add
+
+Privileges:
+  - app_user
+
+Column privileges:
+  + app_user
+
+DDL to be executed:
+--------------------------------------------------
+
+REVOKE UPDATE ON TABLE sometable FROM app_user;
+
+GRANT UPDATE (somecolumn) ON TABLE sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_modify_grant_to_column/diff.sql b/testdata/diff/privilege/issue_324_modify_grant_to_column/diff.sql
new file mode 100644
index 00000000..83414f97
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_modify_grant_to_column/diff.sql
@@ -0,0 +1,3 @@
+REVOKE UPDATE ON TABLE sometable FROM app_user;
+
+GRANT UPDATE (somecolumn) ON TABLE sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_modify_grant_to_column/new.sql b/testdata/diff/privilege/issue_324_modify_grant_to_column/new.sql
new file mode 100644
index 00000000..138f2744
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_modify_grant_to_column/new.sql
@@ -0,0 +1,11 @@
+DO $$
+BEGIN
+    IF NOT EXISTS (SELECT 1 FROM pg_roles WHERE rolname = 'app_user') THEN
+        CREATE ROLE app_user;
+    END IF;
+END $$;
+
+CREATE TABLE sometable (somecolumn text);
+
+GRANT SELECT ON sometable TO app_user;
+GRANT UPDATE (somecolumn) ON sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_modify_grant_to_column/old.sql b/testdata/diff/privilege/issue_324_modify_grant_to_column/old.sql
new file mode 100644
index 00000000..485c2984
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_modify_grant_to_column/old.sql
@@ -0,0 +1,10 @@
+DO $$
+BEGIN
+    IF NOT EXISTS (SELECT 1 FROM pg_roles WHERE rolname = 'app_user') THEN
+        CREATE ROLE app_user;
+    END IF;
+END $$;
+
+CREATE TABLE sometable (somecolumn text);
+
+GRANT SELECT, UPDATE ON sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.json b/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.json
new file mode 100644
index 00000000..a4b780d4
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.json
@@ -0,0 +1,26 @@
+{
+  "version": "1.0.0",
+  "pgschema_version": "1.7.2",
+  "created_at": "1970-01-01T00:00:00Z",
+  "source_fingerprint": {
+    "hash": "1dec24426019fcb5e34cd89432fe55c1f3128e871f5b770263874c4ada106d6f"
+  },
+  "groups": [
+    {
+      "steps": [
+        {
+          "sql": "REVOKE UPDATE ON TABLE sometable FROM app_user;",
+          "type": "privilege",
+          "operation": "alter",
+          "path": "privileges.TABLE.sometable.app_user"
+        },
+        {
+          "sql": "GRANT UPDATE (somecolumn) ON TABLE sometable TO app_user;",
+          "type": "column_privilege",
+          "operation": "create",
+          "path": "column_privileges.TABLE.sometable.somecolumn.app_user"
+        }
+      ]
+    }
+  ]
+}
diff --git a/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.sql b/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.sql
new file mode 100644
index 00000000..83414f97
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.sql
@@ -0,0 +1,3 @@
+REVOKE UPDATE ON TABLE sometable FROM app_user;
+
+GRANT UPDATE (somecolumn) ON TABLE sometable TO app_user;
diff --git a/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.txt b/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.txt
new file mode 100644
index 00000000..cc6e4f2a
--- /dev/null
+++ b/testdata/diff/privilege/issue_324_modify_grant_to_column/plan.txt
@@ -0,0 +1,18 @@
+Plan: 1 to add, 1 to modify.
+
+Summary by type:
+  privileges: 1 to modify
+  column privileges: 1 to add
+
+Privileges:
+  ~ app_user
+
+Column privileges:
+  + app_user
+
+DDL to be executed:
+--------------------------------------------------
+
+REVOKE UPDATE ON TABLE sometable FROM app_user;
+
+GRANT UPDATE (somecolumn) ON TABLE sometable TO app_user;