diff --git a/docs/simple-mode-limitations.md b/docs/simple-mode-limitations.md
index 331b848..d89a1b1 100644
--- a/docs/simple-mode-limitations.md
+++ b/docs/simple-mode-limitations.md
@@ -41,6 +41,22 @@ entry names the ADR that drew the boundary.
 
 ## Table creation (ADR-0029)
 
+- **A simple-mode table always has a primary key; an advanced-mode
+  table need not.** `create table … with pk …` is mandatory in simple
+  mode (ADR-0029) — the bare `with pk` even defaults to `id serial`.
+  Advanced-mode SQL follows standard SQL and permits a *PK-less* table:
+  `create table t (a int)` declares no primary key. This is **not** a
+  storage problem — every ordinary table (STRICT included) carries
+  SQLite's implicit `rowid`, which keys it internally; only a
+  `WITHOUT ROWID` table (which this app never creates) would lack one.
+  So the simple-mode requirement is a *pedagogical* boundary (teach that
+  tables should have a key), not an engine constraint. Consequences in a
+  PK-less table, all handled: `show data … limit` falls back to rowid
+  order (no stable user-facing key to order by); `update` / `delete`
+  still target the affected rows by rowid; and there is no "PK column"
+  to drop — dropping a *declared* PK column is refused in **both** modes
+  (the shared `do_drop_column` guard: *"cannot drop primary-key column
+  …"*).
 - **`create table` declares only primary-key columns.**
   `create table T with pk …` makes every listed column part
   of the primary key; there is no simple-mode syntax for a
diff --git a/tests/it/sql_alter_table.rs b/tests/it/sql_alter_table.rs
index 1d6f360..70c1a97 100644
--- a/tests/it/sql_alter_table.rs
+++ b/tests/it/sql_alter_table.rs
@@ -65,6 +65,50 @@ fn replay_is_refused(script: &str) -> bool {
     matches!(events.last(), Some(AppEvent::ReplayFailed { .. }))
 }
 
+/// Like [`replay_is_refused`] but returns the failure message, so a test
+/// can assert the command was refused *for the expected reason* rather
+/// than e.g. a parse error.
+fn replay_failure_message(script: &str) -> Option<String> {
+    let (project, db, _d) = open();
+    let r = rt();
+    std::fs::write(project.path().join("conv.commands"), script).expect("write script");
+    let events = r.block_on(run_replay(&db, project.path(), "conv.commands"));
+    match events.last() {
+        Some(AppEvent::ReplayFailed { error, .. }) => Some(error.clone()),
+        _ => None,
+    }
+}
+
+#[test]
+fn e2e_alter_drop_primary_key_column_is_refused() {
+    // Issue #19: dropping a PK column must be refused on the advanced
+    // ALTER surface too (it reaches the shared `do_drop_column` guard).
+    let msg = replay_failure_message(
+        "create table T (id int primary key, v text)\n\
+         alter table T drop column id\n",
+    )
+    .expect("dropping a PK column must be refused");
+    assert!(
+        msg.to_lowercase().contains("primary"),
+        "refused for the wrong reason: {msg}"
+    );
+}
+
+#[test]
+fn e2e_alter_drop_compound_primary_key_member_is_refused() {
+    // A member of a *compound* PK is still a PK column, so dropping it is
+    // refused identically (each member reports primary_key = true).
+    let msg = replay_failure_message(
+        "create table T (a int, b int, v text, primary key (a, b))\n\
+         alter table T drop column a\n",
+    )
+    .expect("dropping a compound-PK member must be refused");
+    assert!(
+        msg.to_lowercase().contains("primary"),
+        "refused for the wrong reason: {msg}"
+    );
+}
+
 /// The current user-facing type of column `name` in table `T`.
 fn col_type(db: &Database, r: &tokio::runtime::Runtime, name: &str) -> Option<Type> {
     r.block_on(db.describe_table("T".to_string(), None))