diff --git a/.changeset/quick-icons-taste.md b/.changeset/quick-icons-taste.md
new file mode 100644
index 000000000..95089a253
--- /dev/null
+++ b/.changeset/quick-icons-taste.md
@@ -0,0 +1,5 @@
+---
+'skuba': patch
+---
+
+api: Truncate Buildkite annotations over 1 MiB to resolve `buildkite-agent` crash
diff --git a/package.json b/package.json
index ac8ac3a3e..0fdb3864f 100644
--- a/package.json
+++ b/package.json
@@ -171,6 +171,6 @@
     "entryPoint": "src/index.ts",
     "template": null,
     "type": "package",
-    "version": "8.1.0"
+    "version": "8.2.1"
   }
 }
diff --git a/src/api/buildkite/annotate.test.ts b/src/api/buildkite/annotate.test.ts
index 294a841ca..07dfec2b5 100644
--- a/src/api/buildkite/annotate.test.ts
+++ b/src/api/buildkite/annotate.test.ts
@@ -1,9 +1,11 @@
 import * as execModule from '../../utils/exec';
+import { log } from '../../utils/logging';
 
-import { annotate } from './annotate';
+import { MAX_SIZE, TRUNCATION_WARNING, annotate } from './annotate';
 
 const exec = jest.spyOn(execModule, 'exec');
 const hasCommand = jest.spyOn(execModule, 'hasCommand');
+const mockWarn = jest.spyOn(log, 'warn').mockImplementation(() => undefined);
 
 beforeEach(() => {
   jest.clearAllMocks();
@@ -28,6 +30,8 @@ const setEnvironmentVariables = () => {
 
 describe('annotate', () => {
   const markdown = '**Message**';
+  const endOfMessage = 'EndMessage';
+  const oversizeMarkdown = 'a'.repeat(MAX_SIZE).concat(endOfMessage);
 
   describe.each`
     description                    | opts
@@ -54,6 +58,43 @@ describe('annotate', () => {
       expect(exec).not.toHaveBeenCalled();
     });
 
+    it('warns about truncation when annotation exceeds the maximum size', async () => {
+      setEnvironmentVariables();
+      await annotate(oversizeMarkdown);
+
+      const lastCall = exec.mock.calls[exec.mock.calls.length - 1];
+      if (!lastCall) {
+        throw new Error('Expected exec to have been called at least once');
+      }
+
+      const lastArgument = lastCall[lastCall.length - 1];
+
+      if (typeof lastArgument !== 'string') {
+        throw new Error('Expected the last argument to be a string');
+      }
+
+      expect(lastArgument.endsWith(TRUNCATION_WARNING)).toBe(true);
+    });
+
+    it('logs the full message when annotation is truncated', async () => {
+      setEnvironmentVariables();
+      await annotate(oversizeMarkdown);
+
+      const lastCall = mockWarn.mock.calls[exec.mock.calls.length - 1];
+      if (!lastCall) {
+        throw new Error('Expected log.warn to have been called at least once');
+      }
+
+      const lastArgument = lastCall[lastCall.length - 1];
+
+      if (typeof lastArgument !== 'string') {
+        throw new Error('Expected the last argument to be a string');
+      }
+
+      // Check for the end of message in case there's a failure, entire message isn't printed (it's too large)
+      expect(lastArgument.endsWith(endOfMessage)).toBe(true);
+    });
+
     it('skips when `buildkite-agent` is not present', async () => {
       hasCommand.mockResolvedValue(false);
 
diff --git a/src/api/buildkite/annotate.ts b/src/api/buildkite/annotate.ts
index d3567ff97..179609412 100644
--- a/src/api/buildkite/annotate.ts
+++ b/src/api/buildkite/annotate.ts
@@ -1,4 +1,5 @@
 import { exec, hasCommand } from '../../utils/exec';
+import { log } from '../../utils/logging';
 
 export type AnnotationStyle = 'success' | 'info' | 'warning' | 'error';
 
@@ -24,6 +25,10 @@ interface AnnotationOptions {
   style?: AnnotationStyle;
 }
 
+// Buildkite annotation currently only supports 1MiB of data
+export const MAX_SIZE = 1024 * 1024; // 1MiB in bytes
+export const TRUNCATION_WARNING = '... [Truncated due to size limit]';
+
 /**
  * Asynchronously uploads a Buildkite annotation.
  *
@@ -44,6 +49,16 @@ export const annotate = async (
     return;
   }
 
+  // Check if the annotation exceeds the maximum size
+  let truncatedMarkdown = markdown;
+  if (markdown.length > MAX_SIZE) {
+    // Notify user of truncation, leave space for message
+    const remainingSpace = MAX_SIZE - TRUNCATION_WARNING.length;
+    truncatedMarkdown = markdown.slice(0, remainingSpace) + TRUNCATION_WARNING;
+    // Log full message to the build log
+    log.warn(`Annotation truncated, full message is: ${markdown}`);
+  }
+
   // Always scope to the current Buildkite step.
   const context = [
     opts.scopeContextToStep && process.env.BUILDKITE_STEP_ID,
@@ -59,6 +74,6 @@ export const annotate = async (
     'annotate',
     ...(context ? ['--context', context] : []),
     ...(style ? ['--style', style] : []),
-    markdown,
+    truncatedMarkdown,
   );
 };