diff --git a/packages/agent/src/agent-loop.ts b/packages/agent/src/agent-loop.ts
index 36ba3587e..4e697ed4a 100644
--- a/packages/agent/src/agent-loop.ts
+++ b/packages/agent/src/agent-loop.ts
@@ -49,6 +49,7 @@ import type {
 	AgentMessage,
 	AgentTool,
 	AgentToolResult,
+	AsideMessage,
 	StreamFn,
 } from "./types";
 import { yieldIfDue } from "./utils/yield";
@@ -465,6 +466,23 @@ function cloneAssistantMessageForToolCallCap(message: AssistantMessage): Assista
 	};
 }
 
+/**
+ * Resolve aside entries at the moment the loop is about to inject them. Each entry
+ * is either a ready {@link AgentMessage} or a sync thunk evaluated here so the
+ * producer can make the final inject-or-drop decision (return null) against
+ * up-to-the-injection state — e.g. dropping late diagnostics a newer edit
+ * superseded. Kept sync so it can never stall the loop.
+ */
+function resolveAsides(entries: AsideMessage[] | undefined): AgentMessage[] {
+	if (!entries || entries.length === 0) return [];
+	const out: AgentMessage[] = [];
+	for (const entry of entries) {
+		const message = typeof entry === "function" ? entry() : entry;
+		if (message) out.push(message);
+	}
+	return out;
+}
+
 async function runLoopBody(
 	currentContext: AgentContext,
 	newMessages: AgentMessage[],
@@ -648,13 +666,13 @@ async function runLoopBody(
 			stream.push({ type: "turn_end", message, toolResults });
 
 			const steering = steeringMessagesFromExecution ?? ((await config.getSteeringMessages?.()) || []);
-			const asides = (await config.getAsideMessages?.()) || [];
+			const asides = resolveAsides(await config.getAsideMessages?.());
 			pendingMessages = asides.length > 0 ? [...steering, ...asides] : steering;
 		}
 
 		// Agent would stop here. Drain non-interrupting asides + follow-up messages.
 		await config.onBeforeYield?.();
-		const asideMessages = (await config.getAsideMessages?.()) || [];
+		const asideMessages = resolveAsides(await config.getAsideMessages?.());
 		const followUpMessages = (await config.getFollowUpMessages?.()) || [];
 		if (asideMessages.length > 0 || followUpMessages.length > 0) {
 			// Set as pending so the inner loop processes them before stopping.
diff --git a/packages/agent/src/agent.ts b/packages/agent/src/agent.ts
index 2dbe08de0..3e6a5dfb1 100644
--- a/packages/agent/src/agent.ts
+++ b/packages/agent/src/agent.ts
@@ -33,6 +33,7 @@ import type {
 	AgentState,
 	AgentTool,
 	AgentToolContext,
+	AsideMessage,
 	StreamFn,
 	ToolCallContext,
 } from "./types";
@@ -319,7 +320,7 @@ export class Agent {
 	#onAssistantMessageEvent?: (message: AssistantMessage, event: AssistantMessageEvent) => void;
 	#onHarmonyLeak?: (event: HarmonyAuditEvent) => void | Promise<void>;
 	#onBeforeYield?: () => Promise<void> | void;
-	#asideMessageProvider?: () => AgentMessage[] | Promise<AgentMessage[]>;
+	#asideMessageProvider?: () => AsideMessage[] | Promise<AsideMessage[]>;
 	#telemetry?: AgentLoopConfig["telemetry"];
 	#appendOnlyContext?: AppendOnlyContextManager;
 
@@ -635,7 +636,7 @@ export class Agent {
 	 * completions, late LSP diagnostics) drained at each step boundary. Never
 	 * aborts in-flight tools. See `AgentLoopConfig.getAsideMessages`.
 	 */
-	setAsideMessageProvider(fn: (() => AgentMessage[] | Promise<AgentMessage[]>) | undefined): void {
+	setAsideMessageProvider(fn: (() => AsideMessage[] | Promise<AsideMessage[]>) | undefined): void {
 		this.#asideMessageProvider = fn;
 	}
 
diff --git a/packages/agent/src/types.ts b/packages/agent/src/types.ts
index de32f298d..52db396e0 100644
--- a/packages/agent/src/types.ts
+++ b/packages/agent/src/types.ts
@@ -26,6 +26,14 @@ export type StreamFn = (
 	...args: Parameters<typeof streamSimple>
 ) => AssistantMessageEventStream | Promise<AssistantMessageEventStream>;
 
+/**
+ * An aside entry: a ready {@link AgentMessage}, or a sync thunk evaluated at
+ * injection time that returns the message to inject or `null` to skip it. Thunks
+ * let the producer make the final inject-or-drop decision against current state
+ * (e.g. dropping late diagnostics a newer edit superseded).
+ */
+export type AsideMessage = AgentMessage | (() => AgentMessage | null);
+
 /**
  * Configuration for the agent loop.
  */
@@ -142,7 +150,7 @@ export interface AgentLoopConfig extends SimpleStreamOptions {
 	 * fully stop. Returned messages are appended to the context with normal
 	 * message events and keep the loop running so the model can react.
 	 */
-	getAsideMessages?: () => Promise<AgentMessage[]>;
+	getAsideMessages?: () => Promise<AsideMessage[]>;
 	/**
 	 * Hook fired right before the loop would exit.
 	 *
diff --git a/packages/agent/test/agent-loop.test.ts b/packages/agent/test/agent-loop.test.ts
index 743b1f362..908a568ef 100644
--- a/packages/agent/test/agent-loop.test.ts
+++ b/packages/agent/test/agent-loop.test.ts
@@ -841,6 +841,34 @@ describe("agentLoop with AgentMessage", () => {
 		);
 		expect(sawAsideInContext).toBe(true);
 	});
+
+	it("evaluates aside thunks at injection and skips ones that return null", async () => {
+		const context: AgentContext = { systemPrompt: [""], messages: [], tools: [] };
+		const mock = createMockModel({ responses: [{ content: ["done"] }] });
+		let polls = 0;
+		const config: AgentLoopConfig = {
+			model: mock.model,
+			convertToLlm: identityConverter,
+			// A lazy aside that decides, at injection time, NOT to inject (e.g. superseded).
+			getAsideMessages: async () => {
+				polls++;
+				return [() => null];
+			},
+		};
+
+		const events: AgentEvent[] = [];
+		const stream = agentLoop([createUserMessage("hi")], context, config, undefined, mock.stream);
+		for await (const event of stream) {
+			events.push(event);
+		}
+
+		// The thunk was consulted...
+		expect(polls).toBeGreaterThan(0);
+		// ...but a null result injects nothing and triggers no wasted continuation turn.
+		const userStarts = events.filter(e => e.type === "message_start" && e.message.role === "user");
+		expect(userStarts).toHaveLength(1); // only the original prompt
+		expect(mock.calls).toHaveLength(1);
+	});
 });
 
 it("refreshes tools and system prompt between same-turn model calls", async () => {
diff --git a/packages/coding-agent/src/session/agent-session.ts b/packages/coding-agent/src/session/agent-session.ts
index 51f083502..2a3204943 100644
--- a/packages/coding-agent/src/session/agent-session.ts
+++ b/packages/coding-agent/src/session/agent-session.ts
@@ -1191,7 +1191,7 @@ export class AgentSession {
 		// Background-job completions / late diagnostics are pulled into the run at
 		// each step boundary as non-interrupting asides (see Agent.getAsideMessages),
 		// so they reach the model between requests without waiting for a yield.
-		this.agent.setAsideMessageProvider(() => this.yieldQueue.drainMessages());
+		this.agent.setAsideMessageProvider(() => this.yieldQueue.drainLazy());
 		this.#convertToLlm = config.convertToLlm ?? convertToLlm;
 		this.#rebuildSystemPrompt = config.rebuildSystemPrompt;
 		this.#getMcpServerInstructions = config.getMcpServerInstructions;
diff --git a/packages/coding-agent/src/session/yield-queue.ts b/packages/coding-agent/src/session/yield-queue.ts
index bb92a8e5e..9473c941a 100644
--- a/packages/coding-agent/src/session/yield-queue.ts
+++ b/packages/coding-agent/src/session/yield-queue.ts
@@ -103,21 +103,21 @@ export class YieldQueue {
 	}
 
 	/**
-	 * Build and remove all queued messages, applying each dispatcher's staleness
-	 * filter. No injection side effects — used for pull-based delivery at agent
-	 * step boundaries (see `Agent.setAsideMessageProvider`), so background-job
-	 * completions and late diagnostics reach the model between requests without
-	 * the agent having to stop.
+	 * Snapshot and remove all queued entries, returning one lazy thunk per kind.
+	 * Each thunk applies the dispatcher's staleness filter and builds the batched
+	 * message only when called — so the consumer (the agent loop) decides, at the
+	 * moment it injects, whether the message is still worth delivering (a thunk may
+	 * return null to skip). Background-job completions and late diagnostics reach
+	 * the model between requests without the agent having to stop.
 	 */
-	drainMessages(): AgentMessage[] {
-		const messages: AgentMessage[] = [];
+	drainLazy(): Array<() => AgentMessage | null> {
+		const thunks: Array<() => AgentMessage | null> = [];
 		for (const [kind, dispatcher] of this.#dispatchers) {
 			const entries = this.#drain(kind);
 			if (entries.length === 0) continue;
-			const message = this.#build(kind, dispatcher, entries);
-			if (message) messages.push(message);
+			thunks.push(() => this.#build(kind, dispatcher, entries));
 		}
-		return messages;
+		return thunks;
 	}
 
 	clear(): void {
diff --git a/packages/coding-agent/src/tools/index.ts b/packages/coding-agent/src/tools/index.ts
index 85f832cbe..b70d56684 100644
--- a/packages/coding-agent/src/tools/index.ts
+++ b/packages/coding-agent/src/tools/index.ts
@@ -133,8 +133,9 @@ export interface DeferredDiagnosticsEntry {
 	/** True when any message is error severity. */
 	errored: boolean;
 	/**
-	 * Evaluated at flush time: drop the entry when a newer edit to the same file
-	 * has superseded it, so the model never sees diagnostics for stale content.
+	 * Evaluated at injection time (in the dispatcher's stale check): drop the entry
+	 * when a newer mutation to the same file has superseded it, so the model never
+	 * sees diagnostics for stale content.
 	 */
 	isStale(): boolean;
 }
diff --git a/packages/coding-agent/test/session/yield-queue.test.ts b/packages/coding-agent/test/session/yield-queue.test.ts
index 8264d4ad4..fa749448a 100644
--- a/packages/coding-agent/test/session/yield-queue.test.ts
+++ b/packages/coding-agent/test/session/yield-queue.test.ts
@@ -152,22 +152,45 @@ describe("YieldQueue", () => {
 		expect(harness.streamingMessages.map(messageText)).toEqual(["second", "first"]);
 	});
 
-	test("drainMessages builds non-stale entries, clears the queue, returns nothing on re-drain", async () => {
+	test("drainLazy snapshots+clears immediately but defers build+staleness to the thunk", () => {
 		const harness = createHarness(true);
+		const staleIds = new Set<string>();
 		harness.queue.register<Entry>("items", {
-			isStale: entry => entry.stale === true,
+			isStale: entry => staleIds.has(entry.id),
 			build: entries => userMessage(entries.map(entry => entry.id).join(",")),
 		});
 
-		harness.queue.enqueue("items", { id: "keep" });
-		harness.queue.enqueue("items", { id: "drop", stale: true });
+		harness.queue.enqueue("items", { id: "a" });
+		harness.queue.enqueue("items", { id: "b" });
 
-		const drained = harness.queue.drainMessages();
-		expect(drained.map(messageText)).toEqual(["keep"]);
-		// Pull-based drain has no injection side effects and empties the queue.
+		// Snapshot + clear happens at drain; the queue is emptied immediately.
+		const thunks = harness.queue.drainLazy();
+		expect(thunks).toHaveLength(1);
+		expect(harness.queue.has()).toBe(false);
+
+		// A mutation AFTER drainLazy but BEFORE the thunk runs supersedes "b".
+		staleIds.add("b");
+
+		// The thunk evaluates staleness at call time (injection), dropping "b".
+		const message = thunks[0]!();
+		expect(message && messageText(message)).toBe("a");
+		// No injection side effects from the pull path.
 		expect(harness.streamingMessages).toHaveLength(0);
 		expect(harness.idleBatches).toHaveLength(0);
-		expect(harness.queue.has()).toBe(false);
-		expect(harness.queue.drainMessages()).toEqual([]);
+	});
+
+	test("drainLazy thunk returns null when everything is stale by injection time", () => {
+		const harness = createHarness(true);
+		let stale = false;
+		harness.queue.register<Entry>("items", {
+			isStale: () => stale,
+			build: entries => userMessage(entries.map(entry => entry.id).join(",")),
+		});
+		harness.queue.enqueue("items", { id: "x" });
+
+		const thunks = harness.queue.drainLazy();
+		stale = true; // superseded between drain and injection
+
+		expect(thunks[0]!()).toBeNull();
 	});
 });