diff --git a/packages/core/agent-loop/src/agent.ts b/packages/core/agent-loop/src/agent.ts
index 78614aea25..5eb29db8f6 100644
--- a/packages/core/agent-loop/src/agent.ts
+++ b/packages/core/agent-loop/src/agent.ts
@@ -41,6 +41,8 @@ type Admission =
   | { kind: 'admitted'; messages: UserMessage[] }
   | { kind: 'blocked' }
 
+type StepEndReason = Extract<TurnEndReason, { kind: 'completed' | 'max-tokens' }>
+
 /** Remove adapter-derived values before plugins propose the next request config. */
 function requestProposal(header: EpochHeader): LlmCallConfig {
   if (header.adapterDefaults === undefined) return header.config
@@ -136,15 +138,19 @@ export class ReactLoopAgent implements Agent {
     } while (driver !== this.driverDone)
   }
 
+  /** Report one failure at its live boundary, then preserve it for driver containment. */
+  private throwError(error: unknown): never {
+    const turn = this.phase.kind === 'running' ? this.phase.turn : this.phase.lastTurn
+    const step = this.phase.kind === 'running' ? this.phase.step : 0
+    emitAgentEvent(this.loopCtx, this, 'agent/error', turn, step, error)
+    throw error
+  }
+
   private async kick(): Promise<void> {
     try {
       while (await this.turn()) {}
-    } catch (error: unknown) {
-      if (this.phase.kind !== 'idle') {
-        const turn = this.phase.kind === 'collecting' ? this.phase.lastTurn : this.phase.turn
-        this.setPhase({ kind: 'idle', lastTurn: turn })
-        emitAgentEvent(this.loopCtx, this, 'agent/error', turn, 0, error)
-      }
+    } catch (_error) {
+      // Admission and turn boundaries report before rethrowing; the driver only contains the rejection.
     } finally {
       if (this.phase.kind === 'running') {
         this.setPhase({ kind: 'idle', lastTurn: this.phase.turn })
@@ -176,7 +182,9 @@ export class ReactLoopAgent implements Agent {
 
   /** Admitted input stays unowned until `turn/start` commits. */
   private async turn(): Promise<boolean> {
-    if (this.phase.kind === 'idle') throw new Error(`agent "${this.id}": turn without driver reservation`)
+    if (this.phase.kind === 'idle') {
+      this.throwError(new Error(`agent "${this.id}": turn without driver reservation`))
+    }
     const abort = this.phase.kind === 'collecting' ? this.phase.abort : new AbortController()
     const { signal } = abort
     const lastTurn = this.phase.kind === 'collecting' ? this.phase.lastTurn : this.phase.turn
@@ -191,10 +199,14 @@ export class ReactLoopAgent implements Agent {
     } catch (error: unknown) {
       // oxlint-disable-next-line typescript/no-unnecessary-condition -- cancel may abort while admission awaits
       if (signal.aborted) return this.inbox.hasPending
-      throw error
+      this.throwError(error)
     }
     const turn = ++phase.turn
-    this.session.append('turn/start', { turn })
+    try {
+      this.session.append('turn/start', { turn })
+    } catch (error: unknown) {
+      this.throwError(error)
+    }
     let turnEnds: TurnEndReason | null = null
     try {
       while (true) {
@@ -218,7 +230,7 @@ export class ReactLoopAgent implements Agent {
         }
         admission = await this.admit(false)
         if (admission.kind === 'blocked') {
-          turnEnds = { kind: 'aborted', reason: signal.reason as AgentCancelCause }
+          turnEnds = { kind: 'blocked' }
           return false
         }
         signal.throwIfAborted()
@@ -226,16 +238,27 @@ export class ReactLoopAgent implements Agent {
       }
     } catch (error: unknown) {
       // oxlint-disable-next-line typescript/no-unnecessary-condition -- cancel may abort during any awaited turn operation
-      if (signal.aborted) turnEnds = { kind: 'aborted', reason: signal.reason as AgentCancelCause }
-      else turnEnds = { kind: 'error', error: errorChain(error) }
+      if (signal.aborted) {
+        turnEnds = { kind: 'aborted', reason: signal.reason as AgentCancelCause }
+      } else {
+        turnEnds = {
+          kind: 'error',
+          error: error instanceof LlmError ? error.failure : errorChain(error),
+        }
+        this.throwError(error)
+      }
     } finally {
-      // oxlint-disable-next-line typescript/no-non-null-assertion -- the turn is always ended in this block
-      this.session.append('turn/end', { turn, reason: turnEnds! })
+      try {
+        // oxlint-disable-next-line typescript/no-non-null-assertion -- every exit assigns a turn ending
+        this.session.append('turn/end', { turn, reason: turnEnds! })
+      } catch (error: unknown) {
+        this.throwError(error)
+      }
     }
     return this.inbox.hasPending
   }
 
-  private async step(): Promise<TurnEndReason | null> {
+  private async step(): Promise<StepEndReason | null> {
     if (this.phase.kind !== 'running') throw new Error(`agent "${this.id}": step outside running phase`)
     const { turn, step, abort: { signal } } = this.phase
     signal.throwIfAborted()
@@ -272,7 +295,9 @@ export class ReactLoopAgent implements Agent {
           () => Promise.resolve<RequestErrorAction>(undefined),
         )
         signal.throwIfAborted()
-        if (action?.kind !== 'retry') return { kind: 'error', error: finish.failure }
+        if (action?.kind !== 'retry') {
+          throw new LlmError(finish.failure.message, finish.failure.code, finish.failure)
+        }
         continue
       }
 
diff --git a/packages/core/agent-loop/tests/contract-regressions.spec.ts b/packages/core/agent-loop/tests/contract-regressions.spec.ts
index a19bbfa9de..acfd5b7184 100644
--- a/packages/core/agent-loop/tests/contract-regressions.spec.ts
+++ b/packages/core/agent-loop/tests/contract-regressions.spec.ts
@@ -1,6 +1,6 @@
 import { describe, expect, it } from 'vitest'
 import { Context } from 'cordis'
-import LlmService, { createUserMessage, freezeMessage, CallId, MessageSource, ProviderRequestId, StreamChunk  } from '@deepseek-ai/dsh-llm'
+import LlmService, { createUserMessage, freezeMessage, CallId, LlmError, MessageSource, ProviderRequestId, StreamChunk  } from '@deepseek-ai/dsh-llm'
 import SessionStore, { Session, SessionEvent, SessionId, TurnEndReason, type UserMessage } from '@deepseek-ai/dsh-session'
 import SystemPrompt from '@deepseek-ai/dsh-system-prompt'
 import ToolRegistry, { defineContentToolFixture, type PostToolDecision } from '@deepseek-ai/dsh-tools'
@@ -594,12 +594,20 @@ describe('a finish-error stream chunk ends the turn as error, not completed', ()
     const agent = ctx.agentLoop.create(SessionId('a-finish-error'), { provider: 'mock', model: 'mock' })
 
     const reasons: TurnEndReason[] = []
+    const errors: unknown[] = []
+    ctx.on('agent/error', (_agent, turn, step, error) => {
+      expect({ turn, step }).toEqual({ turn: 1, step: 1 })
+      errors.push(error)
+    })
     ctx.on('session/event', (_s, event) => { if (event.type === 'turn/end') reasons.push(event.data.reason) })
 
     send(agent, 'go')
     await waitForIdle(ctx, agent)
 
     expect(reasons).toEqual([{ kind: 'error', error: failure }])
+    expect(errors).toHaveLength(1)
+    expect(errors[0]).toBeInstanceOf(LlmError)
+    expect((errors[0] as LlmError).failure).toEqual(failure)
 
     const events = [...agent.session.events]
     const turnEnd = events.find(event => event.type === 'turn/end')
@@ -809,6 +817,7 @@ describe('turn and step boundary recovery', () => {
 
     expect(adapter.requests).toHaveLength(1)
     expect(errors.map(error => error.message)).toEqual([
+      'reject first step-end',
       'invariant violated by "@deepseek-ai/dsh-session": turn/end 1 while step 1 is still open',
     ])
     expect(boundaryCounts(agent)).toMatchObject({
@@ -842,6 +851,7 @@ describe('turn and step boundary recovery', () => {
       kind: 'error',
       error: { message: 'provider 500', code: 'SERVER' },
     })
+    expect(threw).toBe(true)
 
     // loop survives: a second turn runs to completion (invariants oracle would
     // throw on its turn/start if turn 1 had been left open).
@@ -1012,7 +1022,9 @@ describe('turn and step boundary recovery', () => {
     expect(e.some(x => x.type === 'step/end')).toBe(true)
     expect(e.some(x => x.type === 'turn/end')).toBe(true)
     expect(e.at(-1)?.type).toBe('turn/end')
-    expect(errors).toEqual([])
+    expect(errors).toHaveLength(1)
+    expect(errors[0]).toBeInstanceOf(LlmError)
+    expect((errors[0] as LlmError).failure).toEqual({ message: 'provider 500', code: 'SERVER' })
 
     // loop survives.
     send(agent, 'again')
diff --git a/packages/core/agent-loop/tests/coverage-edges.spec.ts b/packages/core/agent-loop/tests/coverage-edges.spec.ts
index 5235a81145..650d8493b7 100644
--- a/packages/core/agent-loop/tests/coverage-edges.spec.ts
+++ b/packages/core/agent-loop/tests/coverage-edges.spec.ts
@@ -181,7 +181,10 @@ describe('durable error rendering', () => {
     const turnEnd = agent.session.events.find(e => e.type === 'turn/end')
     expect(turnEnd).toBeDefined()
     if (turnEnd?.type === 'turn/end' && turnEnd.data.reason.kind === 'error') {
-      expect(turnEnd.data.reason.error).toBe('server overloaded')
+      expect(turnEnd.data.reason.error).toEqual({
+        message: 'server overloaded',
+        code: 'RATE_LIMIT',
+      })
     }
   })
 })
diff --git a/packages/core/agent-loop/tests/loop.spec.ts b/packages/core/agent-loop/tests/loop.spec.ts
index 2d856dd3ee..a0b7f1d935 100644
--- a/packages/core/agent-loop/tests/loop.spec.ts
+++ b/packages/core/agent-loop/tests/loop.spec.ts
@@ -1,6 +1,6 @@
 import { describe, expect, it } from 'vitest'
 import { Context } from 'cordis'
-import LlmService, { createUserMessage, CallId, StreamChunk  } from '@deepseek-ai/dsh-llm'
+import LlmService, { createUserMessage, CallId, LlmError, StreamChunk  } from '@deepseek-ai/dsh-llm'
 import SessionStore, { SessionId, TurnEndReason } from '@deepseek-ai/dsh-session'
 import SystemPrompt from '@deepseek-ai/dsh-system-prompt'
 import ToolRegistry, { defineContentToolFixture } from '@deepseek-ai/dsh-tools'
@@ -200,7 +200,9 @@ describe('agent loop', () => {
     await waitForIdle(ctx, agent)
 
     expect(adapter.requests).toHaveLength(0) // the request was never sent
-    expect(errors).toEqual([])
+    expect(errors.map(error => error.message)).toEqual([
+      'prompt variable "{{cwd}}" has no value for this assembly (section "deployment:persona")',
+    ])
     const turnEnd = agent.session.events.find(e => e.type === 'turn/end')
     expect(turnEnd?.type === 'turn/end' && turnEnd.data.reason.kind).toBe('error')
     expect(turnEnd?.type === 'turn/end' && turnEnd.data.reason.kind === 'error'
@@ -346,7 +348,7 @@ describe('agent loop', () => {
     expect(JSON.stringify(adapter.requests[0]?.messages)).toContain('second idle steer')
   })
 
-  it('contains a throwing step observer and carries steering into a replacement turn', async () => {
+  it('stops after a throwing step observer and retains steering until a later wakeup', async () => {
     const adapter = new MockAdapter([textResponse('recovered')])
     const ctx = await harness(adapter)
     const agent = ctx.agentLoop.create(SessionId('failed-steering'), { provider: 'mock', model: 'mock' })
@@ -361,6 +363,13 @@ describe('agent loop', () => {
     send(agent, 'prompt')
     await waitForIdle(ctx, agent)
 
+    expect(adapter.requests).toHaveLength(0)
+    expect(agent.session.events.filter(event => event.type === 'turn/start')).toHaveLength(1)
+    expect(agent.inbox.nextStep).toHaveLength(1)
+
+    send(agent, 'resume')
+    await waitForIdle(ctx, agent)
+
     expect(adapter.requests).toHaveLength(1)
     expect(agent.session.events.filter(event => event.type === 'turn/start')).toHaveLength(2)
     expect(agent.session.events.some(event => event.type === 'steering/message')).toBe(false)
@@ -658,7 +667,7 @@ describe('agent loop', () => {
     send(agent, 'first')
     await waitForIdle(ctx, agent)
     // The first turn failed at step 1 before a model call.
-    expect(errors).toEqual([])
+    expect(errors.map(error => error.message)).toEqual(['boom in pre-step'])
     expect(adapter.requests.length).toBe(0)
     const firstTurnEnd = agent.session.events.find(e => e.type === 'turn/end')
     expect(firstTurnEnd?.type === 'turn/end' && firstTurnEnd.data.reason).toMatchObject({ kind: 'error' })
@@ -1085,20 +1094,24 @@ describe('agent loop', () => {
     const ctx = await harness(adapter)
     const agent = ctx.agentLoop.create(SessionId('a1'), { provider: 'mock', model: 'mock' })
 
-    const errors: Error[] = []
+    const errors: unknown[] = []
     const reasons: TurnEndReason[] = []
     ctx.on('agent/error', (_agent, _turn, _step, error) => {
-      if (error instanceof Error) errors.push(error)
+      errors.push(error)
     })
     ctx.on('session/event', (_s, event) => { if (event.type === 'turn/end') reasons.push(event.data.reason) })
 
     send(agent, 'hi')
     await waitForIdle(ctx, agent)
 
-    expect(errors).toEqual([])
+    expect(errors).toHaveLength(1)
+    expect(errors[0]).toBeInstanceOf(LlmError)
+    expect((errors[0] as LlmError).failure).toEqual({
+      message: 'MockAdapter: script exhausted',
+      code: 'UNKNOWN',
+    })
     expect(reasons[0]).toMatchObject({ kind: 'error' })
-    // The durable failure lives entirely on turn/end.reason (with the failing
-    // step), not a standalone error event.
+    // The durable failure and live relay describe the same failed turn.
     const turnEnd = agent.session.events.find(e => e.type === 'turn/end')
     expect(turnEnd?.type === 'turn/end' && turnEnd.data.reason).toMatchObject({ kind: 'error' })
   })
diff --git a/packages/core/agent-loop/tests/request-reconstruction.spec.ts b/packages/core/agent-loop/tests/request-reconstruction.spec.ts
index d9beaf898e..72524eaa6c 100644
--- a/packages/core/agent-loop/tests/request-reconstruction.spec.ts
+++ b/packages/core/agent-loop/tests/request-reconstruction.spec.ts
@@ -359,7 +359,12 @@ describe('request stability across the loop', () => {
       await waitForIdle(ctx, agent)
 
       expect(agent.session.events.findLast(event => event.type === 'turn/end')).toMatchObject({
-        data: { reason: { kind: 'error', error: failure.message } },
+        data: {
+          reason: {
+            kind: 'error',
+            error: failure instanceof LlmError ? failure.failure : failure.message,
+          },
+        },
       })
       expect(adapter.requests).toHaveLength(0)
     },
diff --git a/packages/core/session/src/types.ts b/packages/core/session/src/types.ts
index 0db4f6d352..32ad54dcd6 100644
--- a/packages/core/session/src/types.ts
+++ b/packages/core/session/src/types.ts
@@ -100,6 +100,8 @@ export interface TurnEndReasonMap {
   completed: { kind: 'completed' }
   /** A cancellation request interrupted the live turn. */
   aborted: { kind: 'aborted'; reason: AgentCancelCause }
+
+  blocked: { kind: 'blocked' }
   /**
    * The turn failed.
    */
diff --git a/packages/goal/goal-session/src/index.ts b/packages/goal/goal-session/src/index.ts
index e65fb41aa6..c65f317657 100644
--- a/packages/goal/goal-session/src/index.ts
+++ b/packages/goal/goal-session/src/index.ts
@@ -300,6 +300,10 @@ export function apply(ctx: Context): void {
           }
           return
         case 'turn/end':
+          if (event.data.reason.kind === 'max-tokens') {
+            disarm(state)
+            return
+          }
           if (event.data.reason.kind !== 'aborted') return
           if (state.attempt?.phase === 'admitted') state.attempt.cancelled = true
           else disarm(state)
diff --git a/packages/goal/goal-session/tests/goal-session.spec.ts b/packages/goal/goal-session/tests/goal-session.spec.ts
index 7cd8090e07..a0bc6defaf 100644
--- a/packages/goal/goal-session/tests/goal-session.spec.ts
+++ b/packages/goal/goal-session/tests/goal-session.spec.ts
@@ -224,15 +224,15 @@ describe('same-session goal driving', () => {
     ['rate limit', new LlmError('slow down', 'RATE_LIMIT')],
     ['request error', new Error('provider broke')],
     ['max tokens', maxTokensResponse('unfinished')],
-  ] as const)('does not attribute a %s to one goal follow-up', async (_label, response) => {
-    const test = await harness(Array.from({ length: 8 }, () => response))
+  ] as const)('disarms automatic continuation after a %s', async (_label, response) => {
+    const test = await harness([response])
     test.ctx.goals.create(test.agent, { objective: 'stop safely', maxGoalRounds: 8 })
 
-    const goal = await waitForGoal(test.ctx, test.agent, current => current?.phase === 'blocked')
+    const goal = await waitForGoal(test.ctx, test.agent, current =>
+      current?.phase === 'active' && current.activation === 'disarmed')
 
-    expect(goal).toMatchObject({ roundsStarted: 8, activation: 'disarmed' })
-    expect(goal?.blockedReason?.code).toBe('round-limit')
-    expect(test.adapter.requests).toHaveLength(8)
+    expect(goal).toMatchObject({ roundsStarted: 1, activation: 'disarmed' })
+    expect(test.adapter.requests).toHaveLength(1)
   })
 
   it('maps a downstream prompt veto to blocked without admitting the round', async () => {
@@ -827,7 +827,7 @@ describe('same-session goal driving', () => {
     expect(warn).not.toHaveBeenCalledWith(expect.stringContaining('goal-session'))
   })
 
-  it('ignores the failed outcome of a round made stale by human work queued at turn start', async () => {
+  it('keeps terminal agent failure disarmed and defers queued human work until another wakeup', async () => {
     const test = await harness([new Error('round one broke'), textResponse('human answer')])
     let queued = false
     test.ctx.on('session/event', (session, event) => {
@@ -841,13 +841,18 @@ describe('same-session goal driving', () => {
     })
     test.ctx.goals.create(test.agent, { objective: 'survive a stale failure', maxGoalRounds: 1 })
 
-    const goal = await waitForGoal(test.ctx, test.agent, current => current?.phase === 'blocked')
+    await waitForGoal(test.ctx, test.agent, current =>
+      current?.phase === 'active' && current.activation === 'disarmed')
+
+    expect(test.adapter.requests).toHaveLength(1)
+    expect(test.agent.inbox.nextTurn).toHaveLength(1)
+
+    test.agent.steer(createUserMessage({ content: [{ type: 'text', text: 'resume after failure' }], source: { kind: 'user' } }))
+    await test.agent.whenIdle()
 
-    // The stale round's turn-error never blocks the goal; only the durable
-    // round budget does, after the interleaved human turn ran.
-    expect(goal?.blockedReason?.code).toBe('round-limit')
     expect(test.adapter.requests).toHaveLength(2)
     expect(requestText(test.adapter.requests[1]!)).toContain('human interleaved')
+    expect(requestText(test.adapter.requests[1]!)).toContain('resume after failure')
   })
 
   it('waits for work queued by a pause observer before considering the next round', async () => {
diff --git a/packages/llm/llm/src/error.ts b/packages/llm/llm/src/error.ts
index c4eb816ff6..fbb8bccca5 100644
--- a/packages/llm/llm/src/error.ts
+++ b/packages/llm/llm/src/error.ts
@@ -93,7 +93,8 @@ export function isQuotaExceededError(detail: string): boolean {
 /**
  * Render a thrown value with its full `cause` chain and AggregateError
  * members, so transport wrappers like undici's `TypeError: fetch failed`
- * surface the underlying failure instead of masking it. Diagnostic-surface
+ * surface the underlying failure instead of masking it. Plain structured
+ * failures render their own data-backed `message`. Diagnostic-surface
  * rendering only (messages, notices, logs) — never parse the result; route on
  * {@link HarnessError.code}.
  * @param value - the caught value (`unknown` in catch clauses).
@@ -109,7 +110,15 @@ export function errorChain(value: unknown): string {
     if (path.has(current)) return '<circular cause>'
     path.add(current)
     try {
-      if (!(current instanceof Error)) return String(current)
+      if (!(current instanceof Error)) {
+        if (typeof current === 'object' && current !== null) {
+          const descriptor = Object.getOwnPropertyDescriptor(current, 'message')
+          if (descriptor !== undefined && 'value' in descriptor && typeof descriptor.value === 'string') {
+            return descriptor.value
+          }
+        }
+        return String(current)
+      }
       const message = current.message === '' ? current.name : current.message
       const members = current instanceof AggregateError && current.errors.length > 0
         ? ` [${current.errors.map(render).join('; ')}]`
diff --git a/packages/llm/llm/tests/service.spec.ts b/packages/llm/llm/tests/service.spec.ts
index 95480b961c..6136daa81a 100644
--- a/packages/llm/llm/tests/service.spec.ts
+++ b/packages/llm/llm/tests/service.spec.ts
@@ -145,6 +145,8 @@ describe('LlmService', () => {
 
   it('errorChain survives non-Error values, hostile coercion, and circular causes', () => {
     expect(errorChain('plain string')).toBe('plain string')
+    expect(errorChain({ message: 'structured provider failure', code: 'SERVER' }))
+      .toBe('structured provider failure')
     expect(errorChain({ toString: () => { throw new Error('hostile') } })).toBe('<unrenderable value>')
     const circular = new Error('outer')
     circular.cause = circular
diff --git a/packages/ui/tui/src/index.ts b/packages/ui/tui/src/index.ts
index 6960886b8e..afcae6bf17 100644
--- a/packages/ui/tui/src/index.ts
+++ b/packages/ui/tui/src/index.ts
@@ -794,7 +794,7 @@ export function createTuiChat(
               liveErrors.delete(key)
               alreadyReported = true
             }
-            const message = reason.error instanceof Error ? reason.error.message : String(reason.error)
+            const message = errorChain(reason.error)
             if (!alreadyReported) appendNotice(message, 'error')
             break
           }
diff --git a/packages/ui/tui/tests/tui.spec.ts b/packages/ui/tui/tests/tui.spec.ts
index a818dbb70c..4a09434cda 100644
--- a/packages/ui/tui/tests/tui.spec.ts
+++ b/packages/ui/tui/tests/tui.spec.ts
@@ -3755,7 +3755,7 @@ describe('pi-tui chat lifecycle and transcript', () => {
     events.session.append('turn/start', { turn: 6 })
     events.session.append('turn/end', {
       turn: 6,
-      reason: { kind: 'error', error: 'structured provider failure' },
+      reason: { kind: 'error', error: { message: 'structured provider failure', code: 'SERVER' } },
     })
     events.session.append('turn/start', { turn: 8 })
     events.session.append('turn/end', {
@@ -3771,6 +3771,7 @@ describe('pi-tui chat lifecycle and transcript', () => {
     expect(events.terminal.output).toContain('durable failure')
     expect(events.terminal.output).toContain('Turn cancelled')
     expect(events.terminal.output).toContain('structured provider failure')
+    expect(events.terminal.output).not.toContain('[object Object]')
     expect(events.terminal.output).toContain('output-token limit')
     expect(events.terminal.output).toContain('previous process ended')
     expect(events.terminal.output).toContain('Turn ended: plugin-policy')