feat: ADR-0036 Phase 2 — validate advanced-mode UPDATE SET literals + retain the value

Mirror Phase 1's capture-at-parse technique on the UPDATE SET assignment
list. build_sql_update calls the new capture_set_literals (data.rs), which
walks the matched tokens (no reparse, no grammar change) and classifies
each top-level `SET col = <rhs>` as a literal (Some, incl. signed numbers)
or an expression (None), using paren depth so a comma inside a function
call or a `where` inside a scalar subquery is not mistaken for a boundary,
and the trailing top-level WHERE is excluded.

Command::SqlUpdate gains set_literals; do_sql_update validates the literals
against their column types via the shared impl_value_for before the still
verbatim update; user_value_for_column reads them so a constraint error
names the offending value. WHERE stays unvalidated; execution and command
identity are unchanged.

Also corrects the stale data.rs header comment (DSL typed slots are wired,
not "deferred") and flips ADR-0036 + README to Phases 1–2 implemented.

Tests: 1934 passing (+4), 0 failed, 0 skipped, 1 ignored; clippy clean.

docs/adr/0036-typed-dml-values-vs-verbatim.md

@@ -11,8 +11,13 @@ consolidating the two modes and a concrete auto-fill difference confirmed
 that even the single-row literal case is **not** identical across modes).
 **Phase 1 implemented 2026-05-26** (`INSERT … VALUES` literal validation +
 offending-value retention; capture-at-parse, no grammar change, execution
-unchanged). Phases 2 (`UPDATE … SET` literals) and 3 (completion
-hinting/highlighting) pending.
+unchanged). **Phase 2 implemented 2026-05-26** (`UPDATE … SET` literal
+validation + offending-value retention; the same capture-at-parse technique
+on the SET assignment list — `capture_set_literals` in `data.rs` —
+classifying each top-level RHS literal-vs-expression, validating literals in
+`do_sql_update`, and reading them in `user_value_for_column`; `WHERE` is not
+validated, execution stays verbatim). Phase 3 (completion
+hinting/highlighting — the only part needing a grammar change) pending.
 
 **Augments** **ADR-0030 §4** and **ADR-0033 §10** — it does **not**
 supersede them and does **not** change the execution model. Advanced-mode
@@ -246,8 +251,19 @@ execution), only its `Result` is used.
   the verbatim insert; the enricher reads them. Covers single- and
   multi-row, with or without `RETURNING`/`ON CONFLICT`, because execution
   is untouched.
-- **Phase 2 — `UPDATE … SET` literal validation** (same technique on the
-  SET assignment list).
+- **Phase 2 (implemented 2026-05-26) — `UPDATE … SET` literal
+  validation.** The same capture-at-parse technique on the SET assignment
+  list: `build_sql_update` calls `capture_set_literals`, which walks the
+  matched tokens (no reparse) and classifies each *top-level* `SET col =
+  <rhs>` into `(col, Some(Value))` for a bare literal (incl. a signed
+  number) or `(col, None)` for an expression — using paren depth so a comma
+  inside a function call or a `where` inside a scalar subquery is never
+  mistaken for an assignment/clause boundary, and so the trailing top-level
+  `WHERE` predicate is excluded. `Command::SqlUpdate` gains a
+  `set_literals` payload; `do_sql_update` validates the literals against
+  their column types (via the shared `impl_value_for`) before the still
+  verbatim update; `user_value_for_column` reads them so a constraint error
+  names the offending value. `WHERE` is deliberately not validated (§2).
 - **Phase 3 — completion hinting / highlighting.** This is the *only*
   part that needs a grammar change: a `Choice(typed-literal-slot,
   sql_expr)` at each value position (reusing the DSL's live

src/app.rs

@@ -3865,6 +3865,7 @@ mod tests {
                 sql: "update t set v = 1".to_string(),
                 target_table: "t".to_string(),
                 returning: false,
+                set_literals: Vec::new(),
             },
             result: crate::db::UpdateResult {
                 rows_affected: 2,
@@ -3897,6 +3898,7 @@ mod tests {
                 sql: "update t set v = 1".to_string(),
                 target_table: "t".to_string(),
                 returning: false,
+                set_literals: Vec::new(),
             },
             result: crate::db::UpdateResult {
                 rows_affected: 1,

src/db.rs

@@ -711,6 +711,10 @@ enum Request {
         source: Option<String>,
         target_table: String,
         returning: bool,
+        /// Captured literal `SET col = <literal>` values (`(col, None)` =
+        /// expression RHS) for app-level type validation before the
+        /// verbatim update (ADR-0036 Phase 2).
+        set_literals: Vec<(String, Option<Value>)>,
         reply: oneshot::Sender<Result<UpdateResult, DbError>>,
     },
     /// Run a grammar-validated SQL `DELETE` (ADR-0033 §1/§7). The
@@ -1506,17 +1510,38 @@ impl Database {
         recv.await.map_err(|_| DbError::WorkerGone)?
     }
 
-    /// Run a validated SQL `UPDATE` and return the affected-row
-    /// count (ADR-0033 §2, sub-phase 3e). `sql` is the
+    /// Run a validated SQL `UPDATE` with **no** captured literals (no
+    /// app-level value validation — the verbatim ADR-0033 path). Used by
+    /// worker-level callers that build the statement directly. The
+    /// runtime, which has a parsed command, uses
+    /// [`Self::run_sql_update_with_literals`] instead so the `SET`
+    /// literals are validated (ADR-0036 Phase 2). `sql` is the
     /// grammar-validated statement text; `source` is the literal
-    /// submitted line for `history.log`; `target_table` is the
-    /// parsed target whose CSV is re-persisted.
+    /// submitted line for `history.log`; `target_table` is the parsed
+    /// target whose CSV is re-persisted.
     pub async fn run_sql_update(
         &self,
         sql: String,
         source: Option<String>,
         target_table: String,
         returning: bool,
+    ) -> Result<UpdateResult, DbError> {
+        self.run_sql_update_with_literals(sql, source, target_table, returning, Vec::new())
+            .await
+    }
+
+    /// As [`Self::run_sql_update`], plus the literal `SET` values captured
+    /// at parse (`(col, None)` = expression RHS) so the worker can
+    /// validate each literal against its column type before the (still
+    /// verbatim) update and the error layer can name the offending value
+    /// (ADR-0036 Phase 2).
+    pub async fn run_sql_update_with_literals(
+        &self,
+        sql: String,
+        source: Option<String>,
+        target_table: String,
+        returning: bool,
+        set_literals: Vec<(String, Option<Value>)>,
     ) -> Result<UpdateResult, DbError> {
         let (reply, recv) = oneshot::channel();
         self.send(Request::RunSqlUpdate {
@@ -1524,6 +1549,7 @@ impl Database {
             source,
             target_table,
             returning,
+            set_literals,
             reply,
         })
         .await?;
@@ -2493,6 +2519,7 @@ fn handle_request(
             source,
             target_table,
             returning,
+            set_literals,
             reply,
         } => {
             snapshot_then(snap, batch, conn, source.as_deref(), reply, || do_sql_update(
@@ -2502,6 +2529,7 @@ fn handle_request(
                 &sql,
                 &target_table,
                 returning,
+                &set_literals,
             ));
         }
         Request::RunSqlDelete {
@@ -8545,10 +8573,27 @@ fn do_sql_update(
     sql: &str,
     target_table: &str,
     returning: bool,
+    set_literals: &[(String, Option<Value>)],
 ) -> Result<UpdateResult, DbError> {
     debug!(sql = %sql, table = %target_table, returning, "sql_update");
     let canonical_table = require_canonical_table(conn, target_table)?;
     let target_table = canonical_table.as_str();
+
+    // ADR-0036 Phase 2: validate each captured `SET col = <literal>`
+    // against its column type BEFORE the (still verbatim) update runs —
+    // sharing the DSL's per-type validators (`impl_value_for`, the same
+    // helper `build_update_sql` uses) for identical wording. Only literal
+    // assignments are checked; expression positions (`None`) and the
+    // `WHERE` predicate are left to the engine (ADR-0036 §2). Execution
+    // below is unchanged (no binding).
+    if set_literals.iter().any(|(_, v)| v.is_some()) {
+        let schema = read_schema(conn, target_table)?;
+        for (col, slot) in set_literals {
+            if let Some(value) = slot {
+                impl_value_for(&schema, col, value)?;
+            }
+        }
+    }
     let tx = conn
         .unchecked_transaction()
         .map_err(DbError::from_rusqlite)?;

src/dsl/command.rs

@@ -442,6 +442,16 @@ pub enum Command {
         /// Whether a `RETURNING` clause matched (ADR-0033 §5,
         /// sub-phase 3g).
         returning: bool,
+        /// Captured literal RHS of each top-level `SET col = <literal>`
+        /// assignment (ADR-0036 Phase 2). `(col, Some(v))` for a bare
+        /// literal (incl. a signed number); `(col, None)` for an
+        /// expression RHS (arithmetic, function call, scalar subquery,
+        /// column ref — nothing static to validate). The worker validates
+        /// the `Some` values against their column types before the (still
+        /// verbatim) update; the error enricher reads them to name the
+        /// offending value. Execution itself is unchanged — these are
+        /// *not* bound. `WHERE` is deliberately excluded (ADR-0036 §2).
+        set_literals: Vec<(String, Option<Value>)>,
     },
     /// A SQL `DELETE` validated by the walker (ADR-0033 §1/§7,
     /// advanced mode). Grammar-as-text: the worker executes `sql`,

src/dsl/grammar/data.rs

@@ -4,17 +4,25 @@
 //! show table), `insert`, `update`, `delete`. The walker route
 //! owns these end-to-end.
 //!
-//! Phase D scope deviation note: ADR-0024's Phase D describes
-//! "full schema awareness" via `DynamicSubgrammar
-//! (column_value_list)` that unfolds typed slots per column. This
-//! milestone lands the data commands at functional parity with
-//! the existing chumsky parser — value slots accept any
-//! literal regardless of column type, with type validation
-//! happening at bind time (matching today's behaviour). The
-//! `DynamicSubgrammar` machinery and schema-cache plumbing are
-//! deferred to a follow-up refinement; the trie shape is
-//! ready to consume them when the schema reference flows
-//! through `parse_command`.
+//! Schema awareness (ADR-0024 §Phase D): the DSL value slots are
+//! wired to `DynamicSubgrammar(column_value_list)` /
+//! `current_column_value` (see `INSERT_VALUES_LIST`,
+//! `insert_first_paren`, `PER_COLUMN_VALUE`), so the schema reference
+//! that flows through `parse_command` unfolds a typed slot per column:
+//! numeric-shape mismatch is caught at parse (`int`/`decimal`/`bool`
+//! slots in `shared.rs`) and the full semantic type (`date` / `shortid`
+//! format) is validated at bind time. So the simple-mode DSL gives data
+//! values per-column feedback end-to-end.
+//!
+//! The advanced-mode SQL DML surface (`build_sql_insert` /
+//! `build_sql_update` below) is a separate path: it executes the
+//! validated statement verbatim (ADR-0030 §4) and is NOT yet wired to
+//! the typed slots. ADR-0036 closes the resulting value-feedback gap
+//! without a grammar change by *capturing* each literal value position
+//! at parse (`capture_literal_rows` / `capture_set_literals`) and
+//! validating it against the column type in the worker — Phase 3 will
+//! later swap that capture for the same typed slots used here, adding
+//! live hints/highlighting.
 
 use crate::dsl::command::{Command, Expr, RowFilter};
 use crate::dsl::grammar::{
@@ -1080,13 +1088,117 @@ fn build_sql_update(path: &MatchedPath, source: &str) -> Result<Command, Validat
         })
         .unwrap_or_default();
     let sql = source.trim().to_string();
+    // Capture the literal RHS of each top-level `SET col = <literal>`
+    // assignment for app-level type validation + error enrichment
+    // (ADR-0036 Phase 2). Purely from the matched tokens — no reparse.
+    let set_literals = capture_set_literals(path);
     Ok(Command::SqlUpdate {
         sql,
         target_table,
         returning: path_has_returning(path),
+        set_literals,
     })
 }
 
+/// Capture the literal RHS of each top-level `SET col = <literal>`
+/// assignment from the matched path (ADR-0036 Phase 2). Returns
+/// `(col, Some(Value))` for a bare-literal RHS (incl. a signed number)
+/// and `(col, None)` for an expression RHS (arithmetic, function call,
+/// scalar subquery, column ref — nothing static to validate). Works
+/// purely from the tokens the walker already matched (no reparse).
+///
+/// Boundaries: the assignment LHS is the `update_set_column` ident (a
+/// role only ever emitted at the top level of an assignment — expression
+/// column refs carry `sql_expr_ident` / `sql_expr_qualified_ref`, so they
+/// are never confused with it). A *depth-0* comma separates assignments;
+/// a *depth-0* `where` / `returning` keyword (or `;` / end of path) ends
+/// the SET list. Parens raise the depth so a comma, `where`, or `=`
+/// inside a function call or scalar subquery on the RHS is never mistaken
+/// for an assignment / clause boundary or the assignment operator.
+fn capture_set_literals(path: &MatchedPath) -> Vec<(String, Option<Value>)> {
+    let mut out: Vec<(String, Option<Value>)> = Vec::new();
+    let mut after_set = false;
+    let mut depth: i32 = 0;
+    // The assignment currently being accumulated: its column name, its
+    // RHS tokens so far, and whether the assignment `=` has been consumed.
+    let mut cur_col: Option<String> = None;
+    let mut cur_rhs: Vec<&MatchedItem> = Vec::new();
+    let mut seen_eq = false;
+
+    // Finalise the pending assignment (if any) into `out`.
+    fn flush(
+        col: &mut Option<String>,
+        rhs: &mut Vec<&MatchedItem>,
+        out: &mut Vec<(String, Option<Value>)>,
+    ) {
+        if let Some(c) = col.take() {
+            out.push((c, classify_value_position(rhs)));
+        }
+        rhs.clear();
+    }
+
+    for item in &path.items {
+        if !after_set {
+            // Scan only the SET list — skip everything up to (and
+            // including) the `set` keyword. The first `update_set_column`
+            // appears after it.
+            if matches!(item.kind, MatchedKind::Word("set")) {
+                after_set = true;
+            }
+            continue;
+        }
+        // A depth-0 `where` / `returning` / `;` ends the SET list.
+        if depth == 0
+            && matches!(
+                item.kind,
+                MatchedKind::Word("where" | "returning") | MatchedKind::Punct(';')
+            )
+        {
+            break;
+        }
+        match &item.kind {
+            MatchedKind::Punct('(') => {
+                depth += 1;
+                if cur_col.is_some() && seen_eq {
+                    cur_rhs.push(item);
+                }
+            }
+            MatchedKind::Punct(')') => {
+                depth -= 1;
+                if cur_col.is_some() && seen_eq {
+                    cur_rhs.push(item);
+                }
+            }
+            MatchedKind::Ident {
+                role: "update_set_column",
+                ..
+            } if depth == 0 => {
+                // A new assignment begins — finalise the previous one.
+                flush(&mut cur_col, &mut cur_rhs, &mut out);
+                cur_col = Some(item.text.clone());
+                seen_eq = false;
+            }
+            MatchedKind::Punct(',') if depth == 0 => {
+                // Assignment separator — finalise the current assignment;
+                // the next `update_set_column` starts the following one.
+                flush(&mut cur_col, &mut cur_rhs, &mut out);
+            }
+            MatchedKind::Punct('=') if depth == 0 && !seen_eq && cur_col.is_some() => {
+                // The assignment operator — consumed, not part of the RHS.
+                seen_eq = true;
+            }
+            _ => {
+                if cur_col.is_some() && seen_eq {
+                    cur_rhs.push(item);
+                }
+            }
+        }
+    }
+    // Finalise the last assignment (ended by `where`/`returning`/`;`/EOF).
+    flush(&mut cur_col, &mut cur_rhs, &mut out);
+    out
+}
+
 /// Build `Command::SqlDelete` from a validated SQL `DELETE`
 /// (ADR-0033 §1/§7). Extracts the target table from the matched
 /// path so the worker re-persists the right CSV and snapshots the

src/runtime.rs

@@ -1583,6 +1583,14 @@ fn user_value_for_column(command: &Command, column: &str) -> Option<crate::dsl::
             let idx = listed_columns.iter().position(|c| c == column)?;
             literal_rows[0].get(idx).cloned().flatten()
         }
+        // ADR-0036 Phase 2: a SQL UPDATE retains its captured `SET`
+        // literals, so a constraint error can name the real value.
+        // Assignments are explicitly named, so (unlike SqlInsert) there is
+        // no positional/multi-row ambiguity — mirror the DSL `Update` case.
+        Command::SqlUpdate { set_literals, .. } => set_literals
+            .iter()
+            .find(|(c, _)| c == column)
+            .and_then(|(_, v)| v.clone()),
         _ => None,
     }
 }
@@ -2270,8 +2278,9 @@ async fn execute_command_typed(
             sql,
             target_table,
             returning,
+            set_literals,
         } => database
-            .run_sql_update(sql, src, target_table, returning)
+            .run_sql_update_with_literals(sql, src, target_table, returning, set_literals)
             .await
             .map(CommandOutcome::Update),
         // A SQL `DELETE` (advanced mode; ADR-0033 §1/§7). Grammar-

tests/friendly_enrichment.rs

@@ -200,6 +200,76 @@ fn enrich_unique_update_resolves_value_from_assignments() {
     });
 }
 
+#[test]
+fn enrich_unique_sql_update_resolves_value_from_set_literals() {
+    // ADR-0036 Phase 2: an advanced-mode SQL `UPDATE` now retains its
+    // `SET` literals, so a UNIQUE violation names the offending value —
+    // closing the error-value gap for advanced mode, mirroring the DSL
+    // `Update` case above. The value flows from the parse-captured
+    // `set_literals` through `user_value_for_column`.
+    let db = db();
+    rt().block_on(async {
+        db.create_table(
+            "Customers".to_string(),
+            vec![
+                ColumnSpec::new("id".to_string(), Type::Int),
+                ColumnSpec::new("name".to_string(), Type::Text),
+            ],
+            vec!["id".to_string()],
+            None,
+        )
+        .await
+        .unwrap();
+        db.insert(
+            "Customers".to_string(),
+            None,
+            vec![Value::Number("1".to_string()), Value::Text("Alice".to_string())],
+            None,
+        )
+        .await
+        .unwrap();
+        db.insert(
+            "Customers".to_string(),
+            None,
+            vec![Value::Number("2".to_string()), Value::Text("Bob".to_string())],
+            None,
+        )
+        .await
+        .unwrap();
+
+        // Advanced-mode SQL: set Bob's id to 1 — collides with Alice.
+        let input = "update Customers set id = 1 where name = 'Bob'";
+        let cmd = parse_command(input).expect("parses as advanced-mode SQL update");
+        let Command::SqlUpdate {
+            sql,
+            target_table,
+            returning,
+            set_literals,
+        } = cmd.clone()
+        else {
+            panic!("expected Command::SqlUpdate, got {cmd:?}");
+        };
+        // The literal `1` is a valid int, so Phase-2 validation passes and
+        // the engine-level UNIQUE violation is what surfaces.
+        let err = db
+            .run_sql_update_with_literals(sql, None, target_table, returning, set_literals)
+            .await
+            .unwrap_err();
+        assert!(matches!(
+            err,
+            DbError::Sqlite { kind: SqliteErrorKind::UniqueViolation, .. }
+        ));
+
+        let facts = enrich_dsl_failure(&db, &cmd, &err).await;
+        assert_eq!(facts.column.as_deref(), Some("id"));
+        assert_eq!(
+            facts.value.as_deref(),
+            Some("1"),
+            "the offending SET value is named (from set_literals)"
+        );
+    });
+}
+
 // ---- NOT NULL ---------------------------------------------------
 
 #[test]

tests/sql_dml_e2e.rs

@@ -114,8 +114,14 @@ fn run_update(
     input: &str,
 ) -> Result<UpdateResult, DbError> {
     match parse_command(input).unwrap_or_else(|e| panic!("parse {input:?}: {e:?}")) {
-        Command::SqlUpdate { sql, target_table, returning } => rt.block_on(
-            db.run_sql_update(sql, Some(input.to_string()), target_table, returning),
+        Command::SqlUpdate { sql, target_table, returning, set_literals } => rt.block_on(
+            db.run_sql_update_with_literals(
+                sql,
+                Some(input.to_string()),
+                target_table,
+                returning,
+                set_literals,
+            ),
         ),
         other => panic!("expected Command::SqlUpdate from {input:?}, got {other:?}"),
     }

tests/sql_update.rs

@@ -8,9 +8,11 @@
 //! across all rows with no rail (ADR-0030 §12).
 
 use rdbms_playground::db::{Database, DbError, UpdateResult};
-use rdbms_playground::dsl::{ColumnSpec, Command, Type, parse_command};
+use rdbms_playground::dsl::{ColumnSpec, Command, Type, Value, parse_command};
+use rdbms_playground::event::AppEvent;
 use rdbms_playground::persistence::Persistence;
 use rdbms_playground::project;
+use rdbms_playground::runtime::run_replay;
 
 fn rt() -> tokio::runtime::Runtime {
     tokio::runtime::Builder::new_current_thread()
@@ -70,9 +72,15 @@ fn run_update(
     input: &str,
 ) -> Result<UpdateResult, DbError> {
     match parse_command(input).expect("parse update") {
-        Command::SqlUpdate { sql, target_table, returning } => {
-            rt.block_on(db.run_sql_update(sql, Some(input.to_string()), target_table, returning))
-        }
+        Command::SqlUpdate { sql, target_table, returning, set_literals } => rt.block_on(
+            db.run_sql_update_with_literals(
+                sql,
+                Some(input.to_string()),
+                target_table,
+                returning,
+                set_literals,
+            ),
+        ),
         other => panic!("expected Command::SqlUpdate, got {other:?}"),
     }
 }
@@ -205,6 +213,114 @@ fn update_appends_literal_line_to_history() {
     assert!(body.contains(input), "history records the literal line: {body:?}");
 }
 
+// =================================================================
+// ADR-0036 Phase 2 — `SET` literal value validation
+// =================================================================
+
+#[test]
+fn sql_update_validates_set_literals_like_the_dsl() {
+    // ADR-0036 Phase 2: advanced-mode SQL `UPDATE` now validates each
+    // literal `SET col = <literal>` value against its column type before
+    // the (still verbatim) update runs, sharing the DSL's per-type
+    // validators. `2025/01/15` is a malformed date (slashes, not dashes):
+    // the DSL update rejects it at bind time, and advanced-mode SQL now
+    // refuses it too (it used to splice the literal into text and let a
+    // STRICT TEXT column accept anything).
+    let (project, db, _dir) = open_project_db();
+    let rt = rt();
+    create_cols(&db, &rt, "t", &[("id", Type::Int), ("d", Type::Date)], &["id"]);
+    seed(&db, &rt, "insert into t (id, d) values (1, '2025-01-15')", "t");
+
+    // SQL path (advanced mode, full replay pipeline) — REJECTS the bad date.
+    std::fs::write(
+        project.path().join("bad.commands"),
+        "update t set d = '2025/01/15' where id = 1\n",
+    )
+    .expect("write script");
+    let events = rt.block_on(run_replay(&db, project.path(), "bad.commands"));
+    assert!(
+        matches!(events.last(), Some(AppEvent::ReplayFailed { .. })),
+        "advanced-mode SQL validates the `date` SET literal and refuses \
+         2025/01/15 (ADR-0036 Phase 2); events: {events:?}"
+    );
+
+    // A well-formed date still updates (the verbatim path is unaffected).
+    std::fs::write(
+        project.path().join("ok.commands"),
+        "update t set d = '2025-02-20' where id = 1\n",
+    )
+    .expect("write script");
+    let ok = rt.block_on(run_replay(&db, project.path(), "ok.commands"));
+    assert!(
+        matches!(ok.last(), Some(AppEvent::ReplayCompleted { count, .. }) if *count == 1),
+        "a well-formed date still updates; events: {ok:?}"
+    );
+}
+
+#[test]
+fn sql_update_captures_set_literal_classification() {
+    // ADR-0036 Phase 2 seam (the "one new seam to keep honest"): each
+    // top-level `SET` RHS is classified — a bare literal (string / signed
+    // number / bool / null) is captured as `Some`, while an expression
+    // (arithmetic / scalar subquery / function call / column ref) is
+    // `None` and left to the engine. Critically, a comma *inside* a
+    // function call and a `where` *inside* a subquery must NOT be mistaken
+    // for an assignment separator / SET-list terminator (paren-depth
+    // guard), and the trailing top-level `WHERE` predicate is not captured.
+    let cmd = parse_command(
+        "update t set a = '2025-01-15', b = price * qty, c = -5, \
+         d = (select max(n) from o where n < 100), e = true, \
+         f = coalesce(g, 0), h = null where id = 7",
+    )
+    .expect("advanced-mode SQL update parses");
+    match cmd {
+        Command::SqlUpdate { set_literals, .. } => {
+            assert_eq!(
+                set_literals,
+                vec![
+                    ("a".to_string(), Some(Value::Text("2025-01-15".to_string()))),
+                    ("b".to_string(), None),
+                    ("c".to_string(), Some(Value::Number("-5".to_string()))),
+                    ("d".to_string(), None),
+                    ("e".to_string(), Some(Value::Bool(true))),
+                    ("f".to_string(), None),
+                    ("h".to_string(), Some(Value::Null)),
+                ],
+                "literals captured; arithmetic / subquery (with inner WHERE) / \
+                 function call (with inner comma) skipped; trailing WHERE excluded",
+            );
+        }
+        other => panic!("expected Command::SqlUpdate, got {other:?}"),
+    }
+}
+
+#[test]
+fn sql_update_validates_every_assignment_not_just_the_first() {
+    // A malformed literal in the *second* assignment is caught — the
+    // validation loop covers every `SET` literal, not only the first
+    // (ADR-0036 Phase 2). The first assignment (`v = 'ok'`) is well-formed.
+    let (project, db, _dir) = open_project_db();
+    let rt = rt();
+    create_cols(
+        &db,
+        &rt,
+        "t",
+        &[("id", Type::Int), ("v", Type::Text), ("d", Type::Date)],
+        &["id"],
+    );
+    seed(&db, &rt, "insert into t (id, v, d) values (1, 'a', '2025-01-01')", "t");
+    std::fs::write(
+        project.path().join("multi.commands"),
+        "update t set v = 'ok', d = '2025/01/15' where id = 1\n",
+    )
+    .expect("write script");
+    let events = rt.block_on(run_replay(&db, project.path(), "multi.commands"));
+    assert!(
+        matches!(events.last(), Some(AppEvent::ReplayFailed { .. })),
+        "the malformed date in the second assignment is caught; events: {events:?}"
+    );
+}
+
 // =================================================================
 // Sub-phase 3g — RETURNING (ADR-0033 §5)
 // =================================================================