diff --git a/src/solidarity.test.ts b/src/solidarity.test.ts
index 67f3229..b653d41 100644
--- a/src/solidarity.test.ts
+++ b/src/solidarity.test.ts
@@ -14,6 +14,8 @@
  * limitations under the License.
  */
 
+import * as nock from "nock";
+
 import { Conclusion, OutputTitle, Solidarity, logger } from "./solidarity";
 
 import { DEFAULT_CONFIGURATION } from "./config";
@@ -21,6 +23,8 @@ import fs from "fs";
 import { parse } from "./parse";
 import { version } from "../package.json";
 
+nock.disableNetConnect();
+
 const payload = JSON.parse(fs.readFileSync("./fixtures/payload.json", "utf8"));
 const failingDIff = parse(
   fs.readFileSync("./fixtures/pull.failing.diff", "utf8")
@@ -110,3 +114,38 @@ test("solidarity should generate correct summary", async () => {
   s.config = DEFAULT_CONFIGURATION;
   expect(s.summary("foo", "1.0.0")).toMatchSnapshot();
 });
+
+test("update should chunk annotations", async () => {
+  const s = new Solidarity({ name: "foo", id: "bar", payload: payload } as any);
+  s.config = DEFAULT_CONFIGURATION;
+  const status = "completed";
+  const conclusion = Conclusion.FAILURE;
+
+  const update = jest.fn();
+  s["context"].github = {
+    checks: {
+      update: update as any,
+    } as any,
+  } as any;
+
+  const output = {
+    title: "title",
+    summary: "summary",
+    annotations: Array.from({ length: 101 }, () => {
+      return {
+        annotation_level: "warning" as const,
+        path: "path",
+        start_line: 0,
+        end_line: 1,
+        message: "message",
+      };
+    }),
+  };
+
+  await s.update(status, conclusion, output);
+
+  expect(update).toBeCalledTimes(3);
+  expect(update.mock.calls[0][0].output.annotations.length).toBe(50);
+  expect(update.mock.calls[1][0].output.annotations.length).toBe(50);
+  expect(update.mock.calls[2][0].output.annotations.length).toBe(1);
+});
diff --git a/src/solidarity.ts b/src/solidarity.ts
index 5035538..81a51ef 100644
--- a/src/solidarity.ts
+++ b/src/solidarity.ts
@@ -189,21 +189,33 @@ export class Solidarity {
   async update(
     status: "queued" | "in_progress" | "completed",
     conclusion?: Conclusion,
-    output?: ChecksUpdateParamsOutput,
-    details_url?: string
+    output?: ChecksUpdateParamsOutput
   ): Promise<void> {
     try {
-      await this.context.github.checks.update({
+      const request = {
         ...this.checkOptions,
         check_run_id: this.checkId as number,
         status,
         conclusion,
         ...(status === "completed" && {
           completed_at: new Date().toISOString(),
+          ...(output && { output }),
         }),
-        ...(output && { output }),
-        details_url,
-      });
+      };
+
+      // There is a limit of 50 annotations per request
+      if (output && output.annotations && output.annotations.length > 50) {
+        await Promise.all(
+          chunk(output.annotations, 50).map((annotations) => {
+            return this.context.github.checks.update({
+              ...request,
+              output: { ...output, annotations },
+            });
+          })
+        );
+      } else {
+        await this.context.github.checks.update(request);
+      }
     } catch (e) {
       this.logger.error({ err: e }, "Failed to update check");
     }
@@ -294,3 +306,13 @@ export class Solidarity {
     });
   }
 }
+
+const chunk = <T>(arr: Array<T>, chunkSize: number): Array<Array<T>> => {
+  return arr.reduce(
+    (previous: any, _: any, index: number, array: Array<T>) =>
+      !(index % chunkSize)
+        ? previous.concat([array.slice(index, index + chunkSize)])
+        : previous,
+    []
+  );
+};