diff --git a/.changeset/tail-forwarding-speaks-up.md b/.changeset/tail-forwarding-speaks-up.md
new file mode 100644
index 00000000000..2a8b773c4a0
--- /dev/null
+++ b/.changeset/tail-forwarding-speaks-up.md
@@ -0,0 +1,7 @@
+---
+"miniflare": patch
+---
+
+Report failures to forward tail events between local dev sessions
+
+When a Worker's tail consumer runs in a separate local dev session and that session becomes unreachable, the failure to deliver tail events was discarded silently. It is now reported as a warning.
diff --git a/fixtures/dev-registry/package.json b/fixtures/dev-registry/package.json
index c3a3b5c9a0d..c55322d5430 100644
--- a/fixtures/dev-registry/package.json
+++ b/fixtures/dev-registry/package.json
@@ -5,7 +5,7 @@
 	"scripts": {
 		"check:types": "tsc --build",
 		"test": "vitest",
-		"test:ci": "vitest run",
+		"test:ci": "vitest run tests/crash-bisect.test.ts",
 		"vite": "vite dev",
 		"wrangler": "wrangler dev"
 	},
diff --git a/fixtures/dev-registry/tests/crash-bisect.test.ts b/fixtures/dev-registry/tests/crash-bisect.test.ts
new file mode 100644
index 00000000000..1969b25b6bf
--- /dev/null
+++ b/fixtures/dev-registry/tests/crash-bisect.test.ts
@@ -0,0 +1,273 @@
+/**
+ * TEMPORARY EXPERIMENT — not for merge.
+ *
+ * Windows CI results so far:
+ *   1  4 arms run concurrently with dev-registry.test.ts     assets 3/8, plain 0/8
+ *   2  same arms isolated, + order swap, + wrangler arm      0/24
+ *   3  2/3/4 concurrent idle sessions, + port fallback       0/17
+ *   4  long-lived victim + one stressor each                 11/12
+ *   5  peer startup vs cpu starvation (rewritten harness)    0/12
+ *   6  round 4's harness verbatim, context captured          13/17
+ *        peer churn 4/5, churn+traffic 4/5, traffic 1/4, cpu 0/3
+ *   7  what exactly is needed, merged timestamped logs
+ *        alpha  7-10 forced restarts, no peer               0/3
+ *        beta   registry entries written/deleted by hand     0/3
+ *        gamma  real peer, SIGKILLed                        3/3
+ *        delta  untouched                                   0/3
+ *
+ * So neither restarting the victim nor feeding it registry churn does anything.
+ * It takes a real peer process that starts, gets wired up, and then dies
+ * abruptly. This round pins down which part of that matters:
+ *
+ *   epsilon  peer killed forcefully, assets + tail consumer   4/5
+ *   zeta     "graceful" stop                                   1/3  (void:
+ *            taskkill /T never actually stopped vite on Windows,
+ *            cleanExits was 0, so this arm just re-ran epsilon)
+ *   eta      peer without assets, killed                       0/3  (11 cycles)
+ *   theta    unrelated assets peer, killed                     0/3  (14 cycles)
+ *
+ * An assets peer on its own is not enough (theta) and a bound peer is not
+ * enough (eta). The only peer that kills the victim is the one that is both an
+ * assets worker and the victim's tail consumer - so the tail path through the
+ * assets RPC proxy hop. Every round so far ran without the fix on
+ * https://github.com/cloudflare/workers-sdk/pull/14993, which makes exactly
+ * that path stop dropping rejections on the floor.
+ *
+ * THIS RUN SITS ON TOP OF THAT FIX. Baseline to beat: epsilon crashed 4/5 reps,
+ * 17 kill cycles. Same arm, 8 reps, plus both negative controls.
+ */
+import childProcess from "node:child_process";
+import * as fs from "node:fs/promises";
+import * as os from "node:os";
+import * as path from "node:path";
+import { resolve } from "node:path";
+import kill from "tree-kill";
+/* eslint-disable workers-sdk/no-vitest-import-expect -- module-scope helpers */
+import { afterAll, describe, onTestFinished, test } from "vitest";
+/* eslint-enable workers-sdk/no-vitest-import-expect */
+
+const cwd = resolve(__dirname, "..");
+const tmpPathBase = path.join(os.tmpdir(), "wrangler-tests");
+const REPS = 8;
+const OBSERVE_MS = 30_000;
+const CRASH =
+	/std::terminate|Fatal uncaught|Received signal|crashed unexpectedly/;
+
+const VICTIM = "exported-handler";
+const PEER = "worker-entrypoint-with-assets";
+const PEER_NO_ASSETS = "worker-entrypoint";
+const PEER_UNRELATED = "exported-handler-with-assets";
+
+// eslint-disable-next-line no-control-regex -- strip terminal colour codes
+const ANSI = /\u001B\[[0-9;]*[A-Za-z]/g;
+
+function stripAnsi(value: string) {
+	return value.replace(ANSI, "");
+}
+
+const results: {
+	arm: string;
+	rep: number;
+	atMs: number | null;
+	cycles: number;
+	cleanExits: number;
+}[] = [];
+let dumped = 0;
+
+function spawnMerged(config: string, registry: string, clock: () => number) {
+	const proc = childProcess.spawn(
+		"pnpm",
+		["vite", "--config", `vite.${config}.config.ts`],
+		{
+			cwd,
+			shell: true,
+			env: { ...process.env, MINIFLARE_REGISTRY_PATH: registry },
+		}
+	);
+	let merged = "";
+	let raw = "";
+	const attach = (stream: "out" | "err", s: NodeJS.ReadableStream | null) => {
+		s?.setEncoding("utf8");
+		s?.on("data", (chunk: string) => {
+			raw += chunk;
+			for (const line of chunk.split(/\r?\n/)) {
+				if (line.trim() !== "") {
+					merged += `+${clock()}ms [${stream}] ${stripAnsi(line)}\n`;
+				}
+			}
+		});
+	};
+	attach("out", proc.stdout);
+	attach("err", proc.stderr);
+
+	let dead = false;
+	const closed = new Promise<void>((res) =>
+		proc.once("close", () => {
+			dead = true;
+			res();
+		})
+	);
+
+	function force() {
+		return new Promise<void>((res) => {
+			if (dead || !proc.pid) {
+				return res();
+			}
+			kill(proc.pid, "SIGKILL", () => res());
+		});
+	}
+
+	/**
+	 * Ask the tree to close rather than shooting it: tree-kill always passes
+	 * /T /F on Windows, which is exactly the abruptness under test.
+	 */
+	function requestStop() {
+		if (dead || !proc.pid) {
+			return;
+		}
+		if (process.platform === "win32") {
+			childProcess.spawn("taskkill", ["/pid", String(proc.pid), "/T"], {
+				stdio: "ignore",
+			});
+		} else {
+			kill(proc.pid, "SIGTERM", () => {});
+		}
+	}
+
+	onTestFinished(force);
+
+	return {
+		force,
+		requestStop,
+		exited: () => dead,
+		log: () => merged,
+		async waitForExit(timeoutMs: number) {
+			await Promise.race([
+				closed,
+				new Promise((r) => setTimeout(r, timeoutMs)),
+			]);
+			return dead;
+		},
+		async ready(timeoutMs = 40_000) {
+			const deadline = Date.now() + timeoutMs;
+			while (Date.now() < deadline && !/Local:/.test(stripAnsi(raw))) {
+				await new Promise((r) => setTimeout(r, 200));
+			}
+			return /Local:/.test(stripAnsi(raw));
+		},
+	};
+}
+
+async function arm(
+	name: string,
+	rep: number,
+	opts: { peer: string; graceful?: boolean }
+) {
+	const registry = await fs.realpath(await fs.mkdtemp(tmpPathBase));
+	onTestFinished(async () => {
+		await fs.rm(registry, { recursive: true, maxRetries: 10 });
+	});
+
+	let t0 = Date.now();
+	const victim = spawnMerged(VICTIM, registry, () => Date.now() - t0);
+	if (!(await victim.ready())) {
+		throw new Error("victim never became ready");
+	}
+	t0 = Date.now();
+
+	let atMs: number | null = null;
+	let watching = true;
+	const watcher = (async () => {
+		while (watching) {
+			if (atMs === null && CRASH.test(victim.log())) {
+				atMs = Date.now() - t0;
+			}
+			await new Promise((r) => setTimeout(r, 200));
+		}
+	})();
+
+	let cycles = 0;
+	let cleanExits = 0;
+	try {
+		while (Date.now() < t0 + OBSERVE_MS) {
+			const peer = spawnMerged(opts.peer, registry, () => 0);
+			await peer.ready();
+			cycles++;
+			await new Promise((r) => setTimeout(r, 2000));
+
+			if (opts.graceful) {
+				peer.requestStop();
+				// A graceful stop that silently fails would leave the peer alive and
+				// make this arm look clean for the wrong reason, so verify, and only
+				// then escalate.
+				if (await peer.waitForExit(10_000)) {
+					cleanExits++;
+				} else {
+					await peer.force();
+				}
+			} else {
+				await peer.force();
+			}
+			await new Promise((r) => setTimeout(r, 1000));
+		}
+	} finally {
+		watching = false;
+		await watcher;
+	}
+
+	const log = victim.log();
+	results.push({ arm: name, rep, atMs, cycles, cleanExits });
+	console.log(
+		`[${name}#${rep}] victim=${
+			atMs === null ? "ok" : `CRASHED at +${atMs}ms`
+		} cycles=${cycles} cleanExits=${cleanExits} restarts=${
+			(log.match(/server restarted/g) ?? []).length
+		}`
+	);
+
+	if (atMs !== null && dumped < 2) {
+		dumped++;
+		const lines = log.split("\n");
+		const i = lines.findIndex((l) => CRASH.test(l));
+		console.log(`::group::[VICTIM LOG] ${name}#${rep}`);
+		console.log(lines.slice(Math.max(0, i - 18), i + 4).join("\n"));
+		console.log("::endgroup::");
+	}
+}
+
+describe.sequential("crash bisect round 8: how the peer dies", () => {
+	afterAll(() => {
+		console.log("\n::group::[BISECT SUMMARY]");
+		for (const a of [...new Set(results.map((r) => r.arm))]) {
+			const rows = results.filter((r) => r.arm === a);
+			const hits = rows.filter((r) => r.atMs !== null);
+			const cycles = rows.reduce((n, r) => n + r.cycles, 0);
+			const clean = rows.reduce((n, r) => n + r.cleanExits, 0);
+			console.log(
+				`  ${a.padEnd(24)} crashed ${hits.length}/${rows.length}  ` +
+					`cycles=${cycles} cleanExits=${clean}` +
+					(hits.length
+						? `  at=[${hits.map((h) => `+${h.atMs}ms`).join(", ")}]`
+						: "")
+			);
+		}
+		console.log("::endgroup::");
+	});
+
+	for (let rep = 1; rep <= REPS; rep++) {
+		test(`epsilon forceful kill #${rep}`, async () => {
+			await arm("epsilon force", rep, { peer: PEER });
+		});
+
+		// Controls only need enough reps to stay comparable with round 8.
+		if (rep <= 3) {
+			test(`eta peer without assets #${rep}`, async () => {
+				await arm("eta no-assets peer", rep, { peer: PEER_NO_ASSETS });
+			});
+
+			test(`theta unrelated peer #${rep}`, async () => {
+				await arm("theta unrelated peer", rep, { peer: PEER_UNRELATED });
+			});
+		}
+	}
+});
diff --git a/packages/miniflare/src/workers/core/dev-registry-proxy.worker.ts b/packages/miniflare/src/workers/core/dev-registry-proxy.worker.ts
index 8fc05d10d87..64e592d5199 100644
--- a/packages/miniflare/src/workers/core/dev-registry-proxy.worker.ts
+++ b/packages/miniflare/src/workers/core/dev-registry-proxy.worker.ts
@@ -161,7 +161,7 @@ export class ExternalServiceProxy extends WorkerEntrypoint<Env, Props> {
 	// Forward tail events to the remote worker via RPC.
 	// Events with rpcMethod==="tail" are filtered out to prevent infinite
 	// recursion (the remote tail() call would itself produce a tail event).
-	tail(events: TraceItem[]) {
+	async tail(events: TraceItem[]) {
 		if (!this._fetcher) {
 			return;
 		}
@@ -176,8 +176,12 @@ export class ExternalServiceProxy extends WorkerEntrypoint<Env, Props> {
 				JSON.stringify(filtered, tailEventsReplacer),
 				tailEventsReviver
 			);
+			// `await` rather than `return`: the RPC rejects when the peer's debug
+			// port has gone away, and returning the promise leaves that rejection
+			// outside this `try`, so it escapes as an unhandled rejection instead of
+			// being reported.
 			// @ts-expect-error .tail is not in the `Fetcher` type but it's a valid RPC call
-			return this._fetcher.tail(serializedEvents);
+			await this._fetcher.tail(serializedEvents);
 		} catch (e) {
 			console.warn(
 				`[dev-registry] Failed to forward tail events to "${
diff --git a/packages/miniflare/test/dev-registry.spec.ts b/packages/miniflare/test/dev-registry.spec.ts
index 5f7714e07f6..7ebfee39158 100644
--- a/packages/miniflare/test/dev-registry.spec.ts
+++ b/packages/miniflare/test/dev-registry.spec.ts
@@ -1787,4 +1787,70 @@ describe.sequential("DevRegistry", () => {
 			{ timeout: 10_000, interval: 100 }
 		);
 	});
+	test("reports a failure to forward tail events to a departed peer", async ({
+		expect,
+	}) => {
+		const unsafeDevRegistryPath = await useTmp();
+
+		const remote = new Miniflare({
+			name: "remote-worker",
+			unsafeDevRegistryPath,
+			compatibilityFlags: ["experimental"],
+			modules: true,
+			script: `
+				import { WorkerEntrypoint } from "cloudflare:workers";
+				export default class extends WorkerEntrypoint {
+					tail() {}
+				}
+			`,
+		});
+		useDispose(remote);
+		await remote.ready;
+
+		const logs: string[] = [];
+		const local = new Miniflare({
+			name: "local-worker",
+			unsafeDevRegistryPath,
+			tails: ["remote-worker"],
+			compatibilityFlags: ["experimental"],
+			modules: true,
+			handleStructuredLogs: ({ message }) => void logs.push(message),
+			script: `
+				export default {
+					fetch() {
+						console.log("tail me");
+						return new Response("ok");
+					}
+				}
+			`,
+		});
+		useDispose(local);
+		await local.ready;
+
+		// Establish the tail forwarding path while the peer is alive.
+		await vi.waitFor(
+			async () => {
+				await (await local.dispatchFetch("http://placeholder")).text();
+				expect(logs.join("\n")).toContain("tail me");
+			},
+			{ timeout: 10_000, interval: 100 }
+		);
+
+		// Drop the peer without letting it deregister, so `local` keeps a registry
+		// entry pointing at a debug port that is no longer accepting connections.
+		// The forwarding RPC now rejects; that rejection must be reported rather
+		// than escaping as an unhandled rejection.
+		await remote.dispose();
+		logs.length = 0;
+
+		await vi.waitFor(
+			async () => {
+				await (await local.dispatchFetch("http://placeholder")).text();
+				expect(logs.join("\n")).toContain(
+					`[dev-registry] Failed to forward tail events to "remote-worker"`
+				);
+			},
+			{ timeout: 10_000, interval: 100 }
+		);
+	});
 });