diff --git a/packages/opencode/src/cli/cmd/tui/context/sync-v2.tsx b/packages/opencode/src/cli/cmd/tui/context/sync-v2.tsx
index f82bb4d962..d9d23999d2 100644
--- a/packages/opencode/src/cli/cmd/tui/context/sync-v2.tsx
+++ b/packages/opencode/src/cli/cmd/tui/context/sync-v2.tsx
@@ -11,21 +11,21 @@ import { createSimpleContext } from "./helper"
 import { useSDK } from "./sdk"
 
 function activeAssistant(messages: SessionMessage[]) {
-  const index = messages.findLastIndex((message) => message.type === "assistant" && !message.time.completed)
+  const index = messages.findIndex((message) => message.type === "assistant" && !message.time.completed)
   if (index < 0) return
   const assistant = messages[index]
   return assistant?.type === "assistant" ? assistant : undefined
 }
 
 function activeCompaction(messages: SessionMessage[]) {
-  const index = messages.findLastIndex((message) => message.type === "compaction")
+  const index = messages.findIndex((message) => message.type === "compaction")
   if (index < 0) return
   const compaction = messages[index]
   return compaction?.type === "compaction" ? compaction : undefined
 }
 
 function activeShell(messages: SessionMessage[], callID: string) {
-  const index = messages.findLastIndex((message) => message.type === "shell" && message.callID === callID)
+  const index = messages.findIndex((message) => message.type === "shell" && message.callID === callID)
   if (index < 0) return
   const shell = messages[index]
   return shell?.type === "shell" ? shell : undefined
@@ -74,7 +74,7 @@ export const { use: useSyncV2, provider: SyncProviderV2 } = createSimpleContext(
       switch (event.type) {
         case "session.next.prompted": {
           update(event.properties.sessionID, (draft) => {
-            draft.push({
+            draft.unshift({
               id: event.id,
               type: "user",
               text: event.properties.prompt.text,
@@ -87,7 +87,7 @@ export const { use: useSyncV2, provider: SyncProviderV2 } = createSimpleContext(
         }
         case "session.next.synthetic":
           update(event.properties.sessionID, (draft) => {
-            draft.push({
+            draft.unshift({
               id: event.id,
               type: "synthetic",
               sessionID: event.properties.sessionID,
@@ -98,7 +98,7 @@ export const { use: useSyncV2, provider: SyncProviderV2 } = createSimpleContext(
           break
         case "session.next.shell.started":
           update(event.properties.sessionID, (draft) => {
-            draft.push({
+            draft.unshift({
               id: event.id,
               type: "shell",
               callID: event.properties.callID,
@@ -120,7 +120,7 @@ export const { use: useSyncV2, provider: SyncProviderV2 } = createSimpleContext(
           update(event.properties.sessionID, (draft) => {
             const currentAssistant = activeAssistant(draft)
             if (currentAssistant) currentAssistant.time.completed = event.properties.timestamp
-            draft.push({
+            draft.unshift({
               id: event.id,
               type: "assistant",
               agent: event.properties.agent,
@@ -143,6 +143,15 @@ export const { use: useSyncV2, provider: SyncProviderV2 } = createSimpleContext(
               currentAssistant.snapshot = { ...currentAssistant.snapshot, end: event.properties.snapshot }
           })
           break
+        case "session.next.step.failed":
+          update(event.properties.sessionID, (draft) => {
+            const currentAssistant = activeAssistant(draft)
+            if (!currentAssistant) return
+            currentAssistant.time.completed = event.properties.timestamp
+            currentAssistant.finish = "error"
+            currentAssistant.error = event.properties.error
+          })
+          break
         case "session.next.text.started":
           update(event.properties.sessionID, (draft) => {
             activeAssistant(draft)?.content.push({ type: "text", text: "" })
@@ -210,7 +219,7 @@ export const { use: useSyncV2, provider: SyncProviderV2 } = createSimpleContext(
             match.time.completed = event.properties.timestamp
           })
           break
-        case "session.next.tool.error":
+        case "session.next.tool.failed":
           update(event.properties.sessionID, (draft) => {
             const match = latestTool(activeAssistant(draft), event.properties.callID)
             if (match?.state.status !== "running") return
@@ -250,7 +259,7 @@ export const { use: useSyncV2, provider: SyncProviderV2 } = createSimpleContext(
           break
         case "session.next.compaction.started":
           update(event.properties.sessionID, (draft) => {
-            draft.push({
+            draft.unshift({
               id: event.id,
               type: "compaction",
               reason: event.properties.reason,
diff --git a/packages/opencode/src/cli/cmd/tui/feature-plugins/system/session-v2.tsx b/packages/opencode/src/cli/cmd/tui/feature-plugins/system/session-v2.tsx
index 7270a9c3b7..73e9b9d435 100644
--- a/packages/opencode/src/cli/cmd/tui/feature-plugins/system/session-v2.tsx
+++ b/packages/opencode/src/cli/cmd/tui/feature-plugins/system/session-v2.tsx
@@ -5,7 +5,7 @@ import { Spinner } from "@tui/component/spinner"
 import { useTheme } from "@tui/context/theme"
 import { useLocal } from "@tui/context/local"
 import { useKeyboard, useRenderer, useTerminalDimensions, type JSX } from "@opentui/solid"
-import type { SyntaxStyle } from "@opentui/core"
+import type { BoxRenderable, SyntaxStyle } from "@opentui/core"
 import { Locale } from "@/util/locale"
 import { LANGUAGE_EXTENSIONS } from "@/lsp/language"
 import path from "path"
@@ -44,6 +44,10 @@ function View(props: { api: TuiPluginApi; sessionID: string }) {
   const messages = createMemo(() => sync.data.messages[props.sessionID] ?? [])
   const renderedMessages = createMemo(() => messages().toReversed())
   const lastAssistant = createMemo(() => renderedMessages().findLast((message) => message.type === "assistant"))
+  const lastUserCreated = (index: number) =>
+    renderedMessages()
+      .slice(0, index)
+      .findLast((message) => message.type === "user")?.time.created
 
   createEffect(() => {
     void sync.session.message.sync(props.sessionID)
@@ -83,6 +87,7 @@ function View(props: { api: TuiPluginApi; sessionID: string }) {
                       last={lastAssistant()?.id === message.id}
                       syntax={syntax()}
                       subtleSyntax={subtleSyntax()}
+                      start={lastUserCreated(index())}
                     />
                   </Match>
                   <Match when={message.type === "synthetic"}>
@@ -294,12 +299,13 @@ function AssistantMessage(props: {
   last: boolean
   syntax: SyntaxStyle
   subtleSyntax: SyntaxStyle
+  start?: number
 }) {
   const { theme } = useTheme()
   const local = useLocal()
   const duration = createMemo(() => {
     if (!props.message.time.completed) return 0
-    return props.message.time.completed - props.message.time.created
+    return props.message.time.completed - (props.start ?? props.message.time.created)
   })
   const model = createMemo(() => {
     const variant = props.message.model.variant ? `/${props.message.model.variant}` : ""
@@ -521,6 +527,7 @@ function InlineTool(props: {
   part: SessionMessageAssistantTool
 }) {
   const { theme } = useTheme()
+  const [margin, setMargin] = createSignal(0)
   const error = createMemo(() => (props.part.state.status === "error" ? props.part.state.error.message : undefined))
   const denied = createMemo(() => {
     const message = error()
@@ -532,21 +539,46 @@ function InlineTool(props: {
     )
   })
   return (
-    <box marginTop={1} paddingLeft={3} flexShrink={0}>
-      <Switch>
-        <Match when={props.spinner}>
-          <Spinner color={theme.text}>{props.children}</Spinner>
-        </Match>
-        <Match when={true}>
-          <text paddingLeft={3} fg={props.complete ? theme.textMuted : theme.text}>
-            <Show fallback={<>~ {props.pending}</>} when={props.complete}>
-              {props.icon} {props.children}
-            </Show>
-          </text>
-        </Match>
-      </Switch>
+    <box
+      marginTop={margin()}
+      paddingLeft={3}
+      flexShrink={0}
+      renderBefore={function () {
+        const el = this as BoxRenderable
+        const parent = el.parent
+        if (!parent) return
+        if (el.height > 1) {
+          setMargin(1)
+          return
+        }
+        const previous = parent.getChildren()[parent.getChildren().indexOf(el) - 1]
+        if (!previous) {
+          setMargin(0)
+          return
+        }
+        if (previous.height > 1 || previous.id.startsWith("text-")) setMargin(1)
+      }}
+    >
+      <box flexDirection="row">
+        <box width={3} flexShrink={0}>
+          <Show
+            when={props.spinner}
+            fallback={<text fg={props.complete ? theme.textMuted : theme.text}>{props.complete ? props.icon : "~"}</text>}
+          >
+            <Spinner color={theme.text} />
+          </Show>
+        </box>
+        <text fg={props.complete ? theme.textMuted : theme.text}>
+          <Show fallback={props.pending} when={props.complete || props.spinner}>
+            {props.children}
+          </Show>
+        </text>
+      </box>
       <Show when={error() && !denied()}>
-        <text fg={theme.error}>{error()}</text>
+        <box flexDirection="row">
+          <box width={3} flexShrink={0} />
+          <text fg={theme.error}>{error()}</text>
+        </box>
       </Show>
     </box>
   )
diff --git a/packages/opencode/src/session/processor.ts b/packages/opencode/src/session/processor.ts
index e2a47f1800..cf1a7e0ae9 100644
--- a/packages/opencode/src/session/processor.ts
+++ b/packages/opencode/src/session/processor.ts
@@ -405,7 +405,7 @@ export const layer: Layer.Layer<
           case "tool-error": {
             const toolCall = yield* readToolCall(value.toolCallId)
             // TODO(v2): Temporary dual-write while migrating session messages to v2 events.
-            EventV2.run(SessionEvent.Tool.Error.Sync, {
+            EventV2.run(SessionEvent.Tool.Failed.Sync, {
               sessionID: ctx.sessionID,
               callID: value.toolCallId,
               error: {
@@ -650,6 +650,17 @@ export const layer: Layer.Layer<
           yield* bus.publish(Session.Event.Error, { sessionID: ctx.sessionID, error })
           return
         }
+        if (!ctx.assistantMessage.summary) {
+          // TODO(v2): Temporary dual-write while migrating session messages to v2 events.
+          EventV2.run(SessionEvent.Step.Failed.Sync, {
+            sessionID: ctx.sessionID,
+            error: {
+              type: error.name,
+              message: errorMessage(e),
+            },
+            timestamp: DateTime.makeUnsafe(Date.now()),
+          })
+        }
         ctx.assistantMessage.error = error
         yield* bus.publish(Session.Event.Error, {
           sessionID: ctx.assistantMessage.sessionID,
diff --git a/packages/opencode/src/session/projectors-next.ts b/packages/opencode/src/session/projectors-next.ts
index 951e3e874f..88f73acf1a 100644
--- a/packages/opencode/src/session/projectors-next.ts
+++ b/packages/opencode/src/session/projectors-next.ts
@@ -161,6 +161,9 @@ export default [
   SyncEvent.project(SessionEvent.Step.Ended.Sync, (db, data, event) => {
     update(db, { id: SessionMessage.ID.make(event.id), type: "session.next.step.ended", data })
   }),
+  SyncEvent.project(SessionEvent.Step.Failed.Sync, (db, data, event) => {
+    update(db, { id: SessionMessage.ID.make(event.id), type: "session.next.step.failed", data })
+  }),
   SyncEvent.project(SessionEvent.Text.Started.Sync, (db, data, event) => {
     update(db, { id: SessionMessage.ID.make(event.id), type: "session.next.text.started", data })
   }),
@@ -181,8 +184,8 @@ export default [
   SyncEvent.project(SessionEvent.Tool.Success.Sync, (db, data, event) => {
     update(db, { id: SessionMessage.ID.make(event.id), type: "session.next.tool.success", data })
   }),
-  SyncEvent.project(SessionEvent.Tool.Error.Sync, (db, data, event) => {
-    update(db, { id: SessionMessage.ID.make(event.id), type: "session.next.tool.error", data })
+  SyncEvent.project(SessionEvent.Tool.Failed.Sync, (db, data, event) => {
+    update(db, { id: SessionMessage.ID.make(event.id), type: "session.next.tool.failed", data })
   }),
   SyncEvent.project(SessionEvent.Reasoning.Started.Sync, (db, data, event) => {
     update(db, { id: SessionMessage.ID.make(event.id), type: "session.next.reasoning.started", data })
diff --git a/packages/opencode/src/v2/session-event.ts b/packages/opencode/src/v2/session-event.ts
index 3af5932f0d..47938dcbed 100644
--- a/packages/opencode/src/v2/session-event.ts
+++ b/packages/opencode/src/v2/session-event.ts
@@ -22,6 +22,11 @@ const Base = {
   sessionID: SessionID,
 }
 
+const Error = Schema.Struct({
+  type: Schema.String,
+  message: Schema.String,
+})
+
 export const AgentSwitched = EventV2.define({
   type: "session.next.agent.switched",
   aggregate: "sessionID",
@@ -128,6 +133,16 @@ export namespace Step {
     },
   })
   export type Ended = Schema.Schema.Type<typeof Ended>
+
+  export const Failed = EventV2.define({
+    type: "session.next.step.failed",
+    aggregate: "sessionID",
+    schema: {
+      ...Base,
+      error: Error,
+    },
+  })
+  export type Failed = Schema.Schema.Type<typeof Failed>
 }
 
 export namespace Text {
@@ -275,23 +290,20 @@ export namespace Tool {
   })
   export type Success = Schema.Schema.Type<typeof Success>
 
-  export const Error = EventV2.define({
-    type: "session.next.tool.error",
+  export const Failed = EventV2.define({
+    type: "session.next.tool.failed",
     aggregate: "sessionID",
     schema: {
       ...Base,
       callID: Schema.String,
-      error: Schema.Struct({
-        type: Schema.String,
-        message: Schema.String,
-      }),
+      error: Error,
       provider: Schema.Struct({
         executed: Schema.Boolean,
         metadata: Schema.Record(Schema.String, Schema.Unknown).pipe(Schema.optional),
       }),
     },
   })
-  export type Error = Schema.Schema.Type<typeof Error>
+  export type Failed = Schema.Schema.Type<typeof Failed>
 }
 
 export const RetryError = Schema.Struct({
@@ -359,6 +371,7 @@ export const All = Schema.Union(
     Shell.Ended,
     Step.Started,
     Step.Ended,
+    Step.Failed,
     Text.Started,
     Text.Delta,
     Text.Ended,
@@ -368,7 +381,7 @@ export const All = Schema.Union(
     Tool.Called,
     Tool.Progress,
     Tool.Success,
-    Tool.Error,
+    Tool.Failed,
     Reasoning.Started,
     Reasoning.Delta,
     Reasoning.Ended,
diff --git a/packages/opencode/src/v2/session-message-updater.ts b/packages/opencode/src/v2/session-message-updater.ts
index ad1aa32e70..d5d5aac7b7 100644
--- a/packages/opencode/src/v2/session-message-updater.ts
+++ b/packages/opencode/src/v2/session-message-updater.ts
@@ -199,6 +199,17 @@ export function update<Result>(adapter: Adapter<Result>, event: SessionEvent.Eve
         )
       }
     },
+    "session.next.step.failed": (event) => {
+      if (currentAssistant) {
+        adapter.updateAssistant(
+          produce(currentAssistant, (draft) => {
+            draft.time.completed = event.data.timestamp
+            draft.finish = "error"
+            draft.error = event.data.error
+          }),
+        )
+      }
+    },
     "session.next.text.started": () => {
       if (currentAssistant) {
         adapter.updateAssistant(
@@ -314,7 +325,7 @@ export function update<Result>(adapter: Adapter<Result>, event: SessionEvent.Eve
         )
       }
     },
-    "session.next.tool.error": (event) => {
+    "session.next.tool.failed": (event) => {
       if (currentAssistant) {
         adapter.updateAssistant(
           produce(currentAssistant, (draft) => {
diff --git a/packages/opencode/src/v2/session-message.ts b/packages/opencode/src/v2/session-message.ts
index 8ec99bc200..94f6b1cac2 100644
--- a/packages/opencode/src/v2/session-message.ts
+++ b/packages/opencode/src/v2/session-message.ts
@@ -152,7 +152,7 @@ export class Assistant extends Schema.Class<Assistant>("Session.Message.Assistan
       write: Schema.Finite,
     }),
   }).pipe(Schema.optional),
-  error: Schema.String.pipe(Schema.optional),
+  error: SessionEvent.Step.Failed.fields.data.fields.error.pipe(Schema.optional),
   time: Schema.Struct({
     created: V2Schema.DateTimeUtcFromMillis,
     completed: V2Schema.DateTimeUtcFromMillis.pipe(Schema.optional),
diff --git a/packages/sdk/js/src/v2/gen/types.gen.ts b/packages/sdk/js/src/v2/gen/types.gen.ts
index caa3d4c767..79ef42d9e1 100644
--- a/packages/sdk/js/src/v2/gen/types.gen.ts
+++ b/packages/sdk/js/src/v2/gen/types.gen.ts
@@ -58,6 +58,7 @@ export type Event =
   | EventSessionNextShellEnded
   | EventSessionNextStepStarted
   | EventSessionNextStepEnded
+  | EventSessionNextStepFailed
   | EventSessionNextTextStarted
   | EventSessionNextTextDelta
   | EventSessionNextTextEnded
@@ -70,7 +71,7 @@ export type Event =
   | EventSessionNextToolCalled
   | EventSessionNextToolProgress
   | EventSessionNextToolSuccess
-  | EventSessionNextToolError
+  | EventSessionNextToolFailed
   | EventSessionNextRetried
   | EventSessionNextCompactionStarted
   | EventSessionNextCompactionDelta
@@ -823,6 +824,7 @@ export type GlobalEvent = {
     | EventSessionNextShellEnded
     | EventSessionNextStepStarted
     | EventSessionNextStepEnded
+    | EventSessionNextStepFailed
     | EventSessionNextTextStarted
     | EventSessionNextTextDelta
     | EventSessionNextTextEnded
@@ -835,7 +837,7 @@ export type GlobalEvent = {
     | EventSessionNextToolCalled
     | EventSessionNextToolProgress
     | EventSessionNextToolSuccess
-    | EventSessionNextToolError
+    | EventSessionNextToolFailed
     | EventSessionNextRetried
     | EventSessionNextCompactionStarted
     | EventSessionNextCompactionDelta
@@ -857,6 +859,7 @@ export type GlobalEvent = {
     | SyncEventSessionNextShellEnded
     | SyncEventSessionNextStepStarted
     | SyncEventSessionNextStepEnded
+    | SyncEventSessionNextStepFailed
     | SyncEventSessionNextTextStarted
     | SyncEventSessionNextTextDelta
     | SyncEventSessionNextTextEnded
@@ -869,7 +872,7 @@ export type GlobalEvent = {
     | SyncEventSessionNextToolCalled
     | SyncEventSessionNextToolProgress
     | SyncEventSessionNextToolSuccess
-    | SyncEventSessionNextToolError
+    | SyncEventSessionNextToolFailed
     | SyncEventSessionNextRetried
     | SyncEventSessionNextCompactionStarted
     | SyncEventSessionNextCompactionDelta
@@ -1973,6 +1976,22 @@ export type SyncEventSessionNextStepEnded = {
   }
 }
 
+export type SyncEventSessionNextStepFailed = {
+  type: "sync"
+  name: "session.next.step.failed.1"
+  id: string
+  seq: number
+  aggregateID: "sessionID"
+  data: {
+    timestamp: number
+    sessionID: string
+    error: {
+      type: string
+      message: string
+    }
+  }
+}
+
 export type SyncEventSessionNextTextStarted = {
   type: "sync"
   name: "session.next.text.started.1"
@@ -2157,9 +2176,9 @@ export type SyncEventSessionNextToolSuccess = {
   }
 }
 
-export type SyncEventSessionNextToolError = {
+export type SyncEventSessionNextToolFailed = {
   type: "sync"
-  name: "session.next.tool.error.1"
+  name: "session.next.tool.failed.1"
   id: string
   seq: number
   aggregateID: "sessionID"
@@ -2710,6 +2729,19 @@ export type EventSessionNextStepEnded = {
   }
 }
 
+export type EventSessionNextStepFailed = {
+  id: string
+  type: "session.next.step.failed"
+  properties: {
+    timestamp: number
+    sessionID: string
+    error: {
+      type: string
+      message: string
+    }
+  }
+}
+
 export type EventSessionNextTextStarted = {
   id: string
   type: "session.next.text.started"
@@ -2870,9 +2902,9 @@ export type EventSessionNextToolSuccess = {
   }
 }
 
-export type EventSessionNextToolError = {
+export type EventSessionNextToolFailed = {
   id: string
-  type: "session.next.tool.error"
+  type: "session.next.tool.failed"
   properties: {
     timestamp: number
     sessionID: string
@@ -3162,7 +3194,10 @@ export type SessionMessageAssistant = {
       write: number
     }
   }
-  error?: string
+  error?: {
+    type: string
+    message: string
+  }
 }
 
 export type SessionMessageCompaction = {