diff --git a/src/logging/sentry.test.ts b/src/logging/sentry.test.ts
index fbbd4bfe2..3e969ca6b 100644
--- a/src/logging/sentry.test.ts
+++ b/src/logging/sentry.test.ts
@@ -3,9 +3,9 @@
  *
  * SPDX-License-Identifier: MIT
  */
-import { captureException } from "@sentry/browser";
+import { captureException, ErrorEvent, init } from "@sentry/browser";
 import { beforeEach, describe, expect, it, vi } from "vitest";
-import { reportError } from "./sentry";
+import { initSentry, reportError } from "./sentry";
 
 vi.mock("@sentry/browser", () => ({
   addBreadcrumb: vi.fn(),
@@ -94,3 +94,63 @@ describe("reportError", () => {
     expect(hint).toBeUndefined();
   });
 });
+
+describe("language server request failure grouping", () => {
+  const fingerprint = (message: string) => {
+    initSentry({ VITE_SENTRY_DSN: dsn });
+    const { beforeSend } = vi.mocked(init).mock.lastCall![0]!;
+    const event: ErrorEvent = {
+      type: undefined,
+      exception: { values: [{ type: "Error", value: message }] },
+    };
+    return (beforeSend!(event, {}) as ErrorEvent).fingerprint;
+  };
+
+  it("groups by request and message", () => {
+    expect(
+      fingerprint(
+        "Request textDocument/completion failed with message: Maximum call stack size exceeded"
+      )
+    ).toEqual([
+      "language-server-request-failed",
+      "textDocument/completion",
+      "Maximum call stack size exceeded",
+    ]);
+  });
+
+  it("ignores which script failed to load", () => {
+    const failure = (url: string) =>
+      fingerprint(
+        `Request initialize failed with message: Failed to execute 'importScripts' on 'WorkerGlobalScope': The script at '${url}' failed to load.`
+      );
+    const fr = failure(
+      "https://python.microbit.org/v/3/workers/pyright-locale-fr-231-e938f9c58b9ac7c8a0c8.worker.js"
+    );
+    expect(fr).toEqual([
+      "language-server-request-failed",
+      "initialize",
+      "Failed to execute 'importScripts' on 'WorkerGlobalScope': The script at '<url>' failed to load.",
+    ]);
+    expect(
+      failure(
+        "https://python.microbit.org/v/3/workers/pyright-locale-en-100-ddc72e6b2c1f5de1a885.worker.js"
+      )
+    ).toEqual(fr);
+  });
+
+  it("separates scripts resolved against a blob URL", () => {
+    expect(
+      fingerprint(
+        "Request initialize failed with message: Failed to execute 'importScripts' on 'WorkerGlobalScope': The script at 'blob:https://python.microbit.org/pyright-locale-en-100-ddc72e6b2c1f5de1a885.worker.js' failed to load."
+      )
+    ).toEqual([
+      "language-server-request-failed",
+      "initialize",
+      "Failed to execute 'importScripts' on 'WorkerGlobalScope': The script at '<blob url>' failed to load.",
+    ]);
+  });
+
+  it("leaves other errors to default grouping", () => {
+    expect(fingerprint("boom")).toBeUndefined();
+  });
+});
diff --git a/src/logging/sentry.ts b/src/logging/sentry.ts
index af5ecfc2d..150078646 100644
--- a/src/logging/sentry.ts
+++ b/src/logging/sentry.ts
@@ -6,6 +6,7 @@
 import {
   addBreadcrumb as sentryAddBreadcrumb,
   captureException as sentryCaptureException,
+  ErrorEvent,
   init as sentryInit,
 } from "@sentry/browser";
 
@@ -31,6 +32,7 @@ export const initSentry = (env: Record<string, string>): string | undefined => {
         // Low consequence and a big chunk of quota.
         "ResizeObserver loop completed with undelivered notifications",
       ],
+      beforeSend: fingerprintLanguageServerRequestFailure,
     });
   } catch (e) {
     console.error(e);
@@ -38,6 +40,33 @@ export const initSentry = (env: Record<string, string>): string | undefined => {
   return dsn;
 };
 
+/**
+ * Every failed language server request is rejected from the same place in
+ * vscode-jsonrpc, so Sentry's stack-based grouping puts unrelated failures
+ * in one issue. Group by the request and the server's message instead.
+ */
+const fingerprintLanguageServerRequestFailure = (
+  event: ErrorEvent
+): ErrorEvent => {
+  const message = event.exception?.values?.[0]?.value;
+  const match =
+    message && /^Request (\S+) failed with message: (.*)$/s.exec(message);
+  if (match) {
+    const [, method, serverMessage] = match;
+    event.fingerprint = [
+      "language-server-request-failed",
+      method,
+      // Script URLs vary by locale and build. Blob URLs stay distinct: the
+      // script's path was resolved against a blob rather than our URL, so
+      // unlike a network failure it can't succeed on retry.
+      serverMessage.replace(/'(blob:)?https?:[^']*'/g, (_, blob) =>
+        blob ? "'<blob url>'" : "'<url>'"
+      ),
+    ];
+  }
+  return event;
+};
+
 /**
  * Report an error to Sentry (if configured) and the console.
  *