diff --git a/docs/adr/0031-advanced-flow-node-executors-and-dag.md b/docs/adr/0031-advanced-flow-node-executors-and-dag.md
new file mode 100644
index 000000000..091676765
--- /dev/null
+++ b/docs/adr/0031-advanced-flow-node-executors-and-dag.md
@@ -0,0 +1,169 @@
+# ADR-0031: Structured control-flow for flows (loop / parallel / try-catch) — native + AI-authored, BPMN as interop
+
+**Status**: Proposed (2026-06-01)
+**Deciders**: ObjectStack Protocol Architects
+**Builds on**: [ADR-0018](./0018-unified-node-action-registry.md) (open action registry — node types are an open vocabulary, executors are the source of truth), [ADR-0019](./0019-approval-as-flow-node.md) (durable-pause node via suspend/resume), [ADR-0010](./0010-nl-to-flow-authoring.md) + [ADR-0011](./0011-actions-as-ai-tools.md) (AI flow authoring — **the design center**)
+**Consumers**: `@objectstack/services/service-automation` (engine + builtin executors), `@objectstack/spec` (`automation/flow.zod.ts`, `automation/bpmn-interop.zod.ts`, `studio/flow-builder.zod.ts`), `../objectui` (flow designer)
+
+---
+
+## TL;DR
+
+The flow designer and protocol expose BPMN-style control nodes — `loop`,
+`parallel_gateway`, `join_gateway`, `boundary_event` — but the engine has **no
+executors** for them (`loop` is a no-op stub). The naive fix is "implement those
+four BPMN token nodes." **This ADR argues against that** and instead adopts
+**structured control-flow constructs** — a `loop` *container*, a `parallel`
+*block*, and `try/catch/retry` — as the **native + AI-authored model**, keeping
+the BPMN gateway/boundary node types in the protocol only as the **import/export
+representation** that maps to/from the structured constructs.
+
+The deciding lens is **AI authoring of flow metadata** ([ADR-0010/0011]). A
+free-form node+edge graph with BPMN gateways/boundary/back-edges is **easy to
+make semantically broken** (orphan joins, unbalanced gateways, deadlocks,
+infinite cycles) — exactly the failure an LLM will produce confidently. A small
+set of **structured constructs is well-formed by construction**, locally
+composable, and statically analyzable — the right substrate for AI.
+
+(Already shipped on this line: `wait` (#1469, durable timer/signal pause) and
+`subflow` (synchronous reusable invoke). `subflow` stays a first-class *reuse*
+primitive — it is **not** the loop mechanism.)
+
+## Context — current state (verified 2026-06-01)
+
+- **The engine is DAG-only.** `registerFlow()` → `detectCycles()` throws on any
+  back-edge ("Only DAG flows are allowed"). A classic inline loop (body → loop
+  back-edge) therefore cannot be registered.
+- **`parallel` is partly free**: `traverseNext()` already runs a node's
+  *unconditional* out-edges via `Promise.all`. The missing piece is a correct
+  **join** (wait-for-all-then-continue-once).
+- **Error handling already exists**: edges carry `type: 'fault'` (route on
+  failure) and `errorHandling.strategy: 'retry'` (exponential backoff). This is
+  already a structured-ish try/catch/retry — closer to what authors want than
+  BPMN boundary events.
+- **BPMN import/export is valued** (`automation/bpmn-interop.zod.ts`). The
+  *protocol* must stay BPMN-complete so external BPM tools round-trip.
+- **The repo is multi-agent.** Core `engine.ts` edits (traversal, cycle
+  detection) must be deliberate and well-sequenced.
+
+## The reframing — why structured beats graph+token for AI authoring
+
+BPMN's gateway/boundary/token model is expressive but notoriously error-prone to
+*author* (for humans, and more so for LLMs). For AI generating flow metadata,
+**structured control-flow constructs** (like a programming language's AST:
+sequence, branch, **loop**, **parallel**, **try/catch**) win on the three things
+AI needs:
+
+1. **Well-formed by construction.** A loop has a defined body + exit; a parallel
+   block's join is implicit at block end; there are no raw back-edges or
+   dangling tokens. An LLM can't easily emit a deadlock or an infinite loop.
+2. **Locally composable.** AI generates a self-contained subtree; variables are
+   in scope; no cross-node token wiring to get wrong.
+3. **Statically analyzable / terminating.** The engine can validate
+   well-formedness and bound iteration — and reject the malformed before run.
+
+Concretely, the per-item-**subflow** loop (an earlier candidate) is *worse* for
+AI: one loop forces **two** flows (parent + body) plus input/output mapping —
+more artifacts, more plumbing to get wrong. A **self-contained inline loop** is
+simpler for AI and humans alike.
+
+## Decision
+
+Adopt **structured control-flow constructs** as the native, AI-authored model:
+
+### 1. Loop — a structured iteration *container* (not a back-edge, not a subflow)
+A `loop` node owns a **bounded body region** (a single-entry/single-exit
+subgraph) plus an "after-loop" continuation. The engine drives iteration over a
+collection (`collection`, `iteratorVariable`) with a **hard max-iteration
+guard**; the body region is scoped, not a raw cycle — so the **DAG invariant for
+ordinary edges is preserved** and termination stays analyzable. (Inline, local,
+AI-friendly.)
+
+### 2. Parallel — a structured *block* with implicit join
+A `parallel` construct declares N branch regions and continues **once when all
+branches complete** — the join is implicit at block end, engine-synchronized
+(per-run, race-free in single-threaded JS). No author-visible `join_gateway`
+arrival-counting node to mis-wire or deadlock. (The existing `Promise.all`
+fan-out is the execution substrate.)
+
+### 3. Errors — structured `try/catch/retry`
+Surface the engine's existing `fault` edge + `errorHandling.retry` as a
+**structured try/catch/retry** attached to a step or block, rather than BPMN
+boundary events. This is the low-code-native error model and is already
+engine-backed.
+
+### 4. DAG invariant — **kept**
+Ordinary step-to-step edges stay acyclic. Iteration and parallel are **structured
+containers**, not cycles or arbitrary token flow — so we get inline loops without
+giving up termination/analyzability.
+
+### 5. BPMN — protocol/interop only, maps onto the constructs
+`parallel_gateway` / `join_gateway` / `boundary_event` and `boundaryConfig` stay
+in the protocol + `bpmn-interop` + designer *rendering* (for import/display).
+**BPMN import maps them onto the structured constructs** (parallel gateways → a
+parallel block; loop markers / multi-instance → a loop container; boundary error
+→ try/catch); export maps back. They are the interchange format, not the native
+authoring model.
+
+### 6. AI authoring — generate structured constructs from the live registry
+Runnable-flow authoring (designer + AI) composes the structured constructs +
+executable nodes from the live action registry (`/api/v1/automation/actions` +
+each node's `configSchema`). Validity is schema-enforced (well-formed
+containers), so AI output is runnable by construction. The full BPMN modeling set
+remains available for interop, not for native authoring.
+
+## Representation — open implementation question (flag, don't over-specify)
+
+The flow model is today a flat `nodes[]` + `edges[]` graph. Two ways to carry
+structured containers; **to be decided in the implementation ADR/PR**:
+
+- **(A) Marker-delimited scoped regions** (recommended starting point): a `loop`
+  / `parallel` node plus a matching scope-end marker; edges inside the scope are
+  the body/branches; the engine validates single-entry/single-exit and executes
+  the region as a unit. Keeps the flat graph the designer + BPMN use; adds
+  structured *semantics* + validation on top.
+- **(B) Nested sub-structure**: the container node carries a nested mini-flow
+  (`config.body`). Cleaner AST, but diverges from the flat graph.
+
+(A) is least disruptive and most BPMN-mappable; (B) is the cleaner long-term AST.
+The choice, plus designer rendering of containers and migration of existing
+flows, is the first task below.
+
+## Consequences
+
+- **Positive**: AI (and humans) author from a small set of constructs that are
+  valid + terminating by construction; no proliferation of error-prone BPMN
+  token nodes; inline loops without breaking the DAG invariant; BPMN
+  import/export preserved as interop; error handling unified on try/catch/retry.
+- **Cost**: bigger than "add four executors" — it introduces structured
+  control-flow into the flow model (spec + engine + designer + a BPMN mapping).
+  Delivered incrementally (below). Existing flat flows keep working (constructs
+  are additive).
+
+## Sequencing (roadmap)
+
+1. **Spec-define the constructs** — `loop` container, `parallel` block,
+   `try/catch/retry`: their schema, `configSchema`, and **well-formedness
+   validation** (single-entry/single-exit regions; bounded loop). Pick
+   representation (A) vs (B).
+2. **Loop container** — engine execution (bounded iteration over a collection) +
+   designer + e2e. *(Highest value; replaces the stub.)*
+3. **Parallel block** — implicit-join execution (per-run synchronization) +
+   designer + e2e.
+4. **Try/catch/retry** — surface the existing `fault` + `retry` as a structured
+   construct in spec + designer.
+5. **BPMN mapping** — `bpmn-interop` import/export ↔ structured constructs.
+
+## Non-goals / deferred
+
+- Author-visible low-level BPMN `parallel_gateway` / `join_gateway` /
+  `boundary_event` as the *native* model (kept for interop only).
+- Relaxing the DAG invariant to allow arbitrary cycles (loops are structured
+  containers instead).
+- Runtime BPMN boundary events (timer/signal) — interop representation retained.
+
+## Already shipped this line of work
+
+- `wait` executor (#1469) — durable timer/signal pause.
+- `subflow` executor — synchronous reusable invoke (depth-guarded; nested pause
+  → clear error). Remains a reuse primitive, orthogonal to the loop container.
diff --git a/examples/app-showcase/src/objects/account.object.ts b/examples/app-showcase/src/objects/account.object.ts
index 1ad83cdbf..52a35c4f8 100644
--- a/examples/app-showcase/src/objects/account.object.ts
+++ b/examples/app-showcase/src/objects/account.object.ts
@@ -48,6 +48,8 @@ export const Account = ObjectSchema.create({
       label: 'Account Lifecycle',
       description: 'Accounts move prospect → active → churned, and can be reactivated.',
       field: 'status',
+      // Transitions are validated on update; insert sets the initial state.
+      events: ['update'] as const,
       message: 'Invalid account lifecycle transition.',
       transitions: {
         prospect: ['active', 'churned'],
diff --git a/examples/app-showcase/src/objects/project.object.ts b/examples/app-showcase/src/objects/project.object.ts
index 3193dfee7..069cf5a0a 100644
--- a/examples/app-showcase/src/objects/project.object.ts
+++ b/examples/app-showcase/src/objects/project.object.ts
@@ -74,6 +74,9 @@ export const Project = ObjectSchema.create({
       label: 'Project Status Flow',
       description: 'Projects progress through valid status transitions.',
       field: 'status',
+      // State machines validate *transitions*, so they run on update only —
+      // an insert sets the initial state (constrained by the select options).
+      events: ['update'] as const,
       message: 'Invalid project status transition.',
       transitions: {
         planned: ['active', 'cancelled'],
@@ -83,5 +86,24 @@ export const Project = ObjectSchema.create({
         cancelled: ['planned'],
       },
     },
+    {
+      // Advisory (severity: 'warning') state machine — demonstrates a soft
+      // transition guard: health should escalate/de-escalate one step at a
+      // time (green↔yellow↔red). A jump (e.g. green→red) is *flagged* (logged
+      // server-side) but NOT blocked, unlike the error-severity status flow.
+      type: 'state_machine' as const,
+      name: 'project_health_progression',
+      label: 'Project Health Progression (advisory)',
+      description: 'Health should change one step at a time; skips are warned, not blocked.',
+      field: 'health',
+      events: ['update'] as const,
+      severity: 'warning' as const,
+      message: 'Health changed by more than one step — confirm this is intentional.',
+      transitions: {
+        green: ['yellow'],
+        yellow: ['green', 'red'],
+        red: ['yellow'],
+      },
+    },
   ],
 });
diff --git a/examples/app-showcase/src/objects/task.object.ts b/examples/app-showcase/src/objects/task.object.ts
index 85eb544ba..927bc5b43 100644
--- a/examples/app-showcase/src/objects/task.object.ts
+++ b/examples/app-showcase/src/objects/task.object.ts
@@ -66,6 +66,8 @@ export const Task = ObjectSchema.create({
       label: 'Task Status Flow',
       description: 'Tasks move forward through the board (reopen allowed from Done).',
       field: 'status',
+      // Transitions are validated on update; insert sets the initial state.
+      events: ['update'] as const,
       message: 'Invalid task status transition.',
       transitions: {
         backlog: ['todo'],