diff --git a/packages/agent/src/agent-loop.ts b/packages/agent/src/agent-loop.ts
index 3a4f6c25d..1dafe1dc9 100644
--- a/packages/agent/src/agent-loop.ts
+++ b/packages/agent/src/agent-loop.ts
@@ -2298,6 +2298,23 @@ export interface SyntheticToolResultDetails {
 	upstreamError?: string;
 }
 
+/**
+ * Narrow an {@link AgentMessage} to a synthetic {@link ToolResultMessage} —
+ * a tool_result emitted for a tool call the assistant never invoked (see
+ * {@link SyntheticToolResultDetails}). Consumers use this to look past the
+ * placeholder pairing back to the assistant turn that produced it, e.g.
+ * `AgentSession.retry()` walking back over the synthetic results a
+ * stalled/aborted mid-tool-call turn leaves behind.
+ */
+export function isSyntheticToolResultMessage(
+	message: AgentMessage | undefined,
+): message is ToolResultMessage<SyntheticToolResultDetails> {
+	return (
+		message?.role === "toolResult" &&
+		(message.details as SyntheticToolResultDetails | undefined)?.__synthetic === true
+	);
+}
+
 function syntheticDetailsFor(
 	reason: "aborted" | "error" | "skipped" | "length",
 	errorMessage: string | undefined,
diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index c40d5b070..c5fa9fa4c 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -147,6 +147,7 @@
 - Fixed dynamic model discovery refreshes dropping provider-level compatibility overrides from `models.yml` ([#6041](https://github.com/can1357/oh-my-pi/issues/6041)).
 - Fixed a startup crash that locked users out of the app when `prewalk.enabled` was set but the prewalk hand-off target (default `@smol`) had no configured API key; prewalk now stays unarmed with a warning instead of aborting startup ([#6064](https://github.com/can1357/oh-my-pi/issues/6064)).
 - Fixed in-progress aborts awaiting `session_stop` extension handlers whose results would be discarded ([#6134](https://github.com/can1357/oh-my-pi/issues/6134)).
+- Fixed `/retry` reporting "Nothing to retry" after a stream stalled or aborted mid-tool-call, where a synthetic tool result appended for the un-run tool call shadowed the failed assistant turn ([#6056](https://github.com/can1357/oh-my-pi/issues/6056)).
 
 ## [17.0.5] - 2026-07-18
 
diff --git a/packages/coding-agent/src/session/agent-session.ts b/packages/coding-agent/src/session/agent-session.ts
index acd2451e8..a7429799f 100644
--- a/packages/coding-agent/src/session/agent-session.ts
+++ b/packages/coding-agent/src/session/agent-session.ts
@@ -37,6 +37,7 @@ import {
 	type CompactionSummaryMessage,
 	countTokens,
 	createToolScopedAbortReason,
+	isSyntheticToolResultMessage,
 	resolveTelemetry,
 	type StreamFn,
 	TERMINAL_TOOL_RESULT_ABORT_REASON,
@@ -15758,20 +15759,40 @@ export class AgentSession {
 	/**
 	 * Manually retry the last failed assistant turn.
 	 * Removes the error message from agent state and re-attempts with a fresh retry budget.
+	 *
+	 * A stream that stalls or aborts mid-tool-call ends the turn with
+	 * `stopReason: "error" | "aborted"` and then appends one synthetic
+	 * {@link isSyntheticToolResultMessage tool_result} per emitted tool call to
+	 * preserve the provider's tool_use/tool_result pairing (see
+	 * `createAbortedToolResult` in `agent-loop.ts`). Those placeholders trail the
+	 * failed assistant turn, so the retry lookback walks back over them before
+	 * checking the assistant message; it strips both the placeholders and the
+	 * failed turn before re-attempting.
+	 *
 	 * @returns true if retry was initiated, false if no failed turn to retry or agent is busy
 	 */
 	async retry(): Promise<boolean> {
 		if (this.isStreaming || this.isCompacting || this.isRetrying) return false;
 
 		const messages = this.agent.state.messages;
-		const lastMsg = messages[messages.length - 1];
+
+		// Walk back past trailing synthetic tool_result placeholders emitted for
+		// tool calls that never ran because the turn stalled/aborted mid-tool-call.
+		// They shadow the failed assistant turn from the single-message lookback.
+		let turnEnd = messages.length;
+		while (turnEnd > 0 && isSyntheticToolResultMessage(messages[turnEnd - 1])) {
+			turnEnd--;
+		}
+
+		const lastMsg = messages[turnEnd - 1];
 		if (lastMsg?.role !== "assistant") return false;
 
 		const assistantMsg = lastMsg as AssistantMessage;
 		if (assistantMsg.stopReason !== "error" && assistantMsg.stopReason !== "aborted") return false;
 
-		// Remove the failed/aborted assistant message (same as auto-retry does before re-attempting)
-		this.agent.replaceMessages(messages.slice(0, -1));
+		// Remove the failed/aborted assistant message plus its synthetic tool
+		// results (same as auto-retry does before re-attempting).
+		this.agent.replaceMessages(messages.slice(0, turnEnd - 1));
 
 		// Reset retry budget for a fresh attempt
 		this.#retryAttempt = 0;
diff --git a/packages/coding-agent/test/agent-session-manual-retry.test.ts b/packages/coding-agent/test/agent-session-manual-retry.test.ts
index d90820262..5bc94f805 100644
--- a/packages/coding-agent/test/agent-session-manual-retry.test.ts
+++ b/packages/coding-agent/test/agent-session-manual-retry.test.ts
@@ -115,4 +115,62 @@ describe("AgentSession manual retry", () => {
 		expect(mock.calls.length).toBe(1);
 		expect(lastAgentMessage(session).content).toContainEqual({ type: "text", text: "already done" });
 	});
+
+	it("retries past synthetic tool results left by a mid-tool-call stream stall", async () => {
+		const model = getBundledModel("anthropic", "claude-sonnet-4-5");
+		if (!model) {
+			throw new Error("Expected bundled Anthropic test model to exist");
+		}
+
+		// First turn stalls mid-tool-call: the assistant emits a `write` tool call
+		// but the stream ends with an error before it runs, so `stopReason: "error"`.
+		// The agent loop then appends a synthetic tool_result for the un-run call,
+		// which trails the failed assistant turn in agent state.
+		const mock = createMockModel({
+			responses: [
+				{
+					content: [{ type: "toolCall", name: "write", arguments: { path: "plan.md", content: "x" } }],
+					stopReason: "error",
+					errorMessage: "OpenAI completions stream stalled while waiting for the next event",
+				},
+				{ content: ["recovered after stalled tool call"], stopReason: "stop" },
+			],
+		});
+		const agent = new Agent({
+			getApiKey: model => `${model.provider}-test-key`,
+			initialState: {
+				model,
+				systemPrompt: ["Test"],
+				tools: [],
+				messages: [],
+			},
+			streamFn: mock.stream,
+		});
+		session = new AgentSession({
+			agent,
+			sessionManager: SessionManager.inMemory(),
+			settings: Settings.isolated({ "compaction.enabled": false, "retry.enabled": false }),
+			modelRegistry: new ModelRegistry(authStorage),
+		});
+		session.subscribe(() => {});
+
+		await session.prompt("write the plan");
+		await session.waitForIdle();
+
+		// The failed assistant turn is shadowed by a trailing synthetic tool_result.
+		const messages = session.agent.state.messages;
+		expect(messages.at(-1)?.role).toBe("toolResult");
+		const failedAssistant = messages.findLast(m => m.role === "assistant") as AssistantMessage;
+		expect(failedAssistant.stopReason).toBe("error");
+
+		await expect(session.retry()).resolves.toBe(true);
+		await session.waitForIdle();
+
+		expect(mock.calls.length).toBe(2);
+		expect(lastAgentMessage(session).stopReason).toBe("stop");
+		expect(lastAgentMessage(session).content).toContainEqual({
+			type: "text",
+			text: "recovered after stalled tool call",
+		});
+	});
 });