diff --git a/packages/http/src/mocker/__tests__/HttpMocker.spec.ts b/packages/http/src/mocker/__tests__/HttpMocker.spec.ts
index 9ad103788..65a5d33f4 100644
--- a/packages/http/src/mocker/__tests__/HttpMocker.spec.ts
+++ b/packages/http/src/mocker/__tests__/HttpMocker.spec.ts
@@ -522,6 +522,24 @@ describe('mocker', () => {
             it('should return the example key', () =>
               assertRight(eitherResponse, response => expect(response.body).toHaveProperty('name', 'Clark')));
 
+            describe('when the property has anyOf and an examples value', () => {
+              const eitherResponseWithAnyOfExample = mockResponseWithSchema({
+                type: 'object',
+                properties: {
+                  title: {
+                    anyOf: [{ type: 'string' }, { type: 'null' }],
+                    title: 'Title',
+                    examples: ['Some kind of title'],
+                  },
+                },
+              });
+
+              it('should use the property example', () =>
+                assertRight(eitherResponseWithAnyOfExample, response =>
+                  expect(response.body).toHaveProperty('title', 'Some kind of title')
+                ));
+            });
+
             describe('and also a default key', () => {
               const eitherResponseWithDefault = mockResponseWithSchema({
                 type: 'object',
diff --git a/packages/http/src/mocker/generator/JSONSchema.ts b/packages/http/src/mocker/generator/JSONSchema.ts
index dc0071a12..d404d5e57 100644
--- a/packages/http/src/mocker/generator/JSONSchema.ts
+++ b/packages/http/src/mocker/generator/JSONSchema.ts
@@ -77,10 +77,13 @@ export function generate(
         // @ts-ignore
         () => {
           if (seed) {
-            JSONSchemaFaker.option('random', seedrandom(seed))
+            JSONSchemaFaker.option('random', seedrandom(seed));
           }
           // @ts-ignore
-          return sortSchemaAlphabetically(JSONSchemaFaker.generate({ ...cloneDeep(updatedSource), __bundled__: bundle }))
+          return sortSchemaAlphabetically(
+            // @ts-ignore
+            JSONSchemaFaker.generate({ ...cloneDeep(updatedSource), __bundled__: bundle })
+          );
         },
         toError
       )
@@ -111,8 +114,11 @@ export function sortSchemaAlphabetically(source: any): any {
 }
 
 export function generateStatic(operation: IHttpOperation, source: JSONSchema): Either<Error, unknown> {
+  const schemaWithPromotedUnionExamples = cloneDeep(source);
+  promoteUnionExamples(schemaWithPromotedUnionExamples);
+
   return pipe(
-    tryCatch(() => sampler.sample(source, { ticks: 2500 }, operation), toError),
+    tryCatch(() => sampler.sample(schemaWithPromotedUnionExamples, { ticks: 2500 }, operation), toError),
     E.mapLeft(err => {
       if (err instanceof sampler.SchemaSizeExceededError) {
         return new SchemaTooComplexGeneratorError(operation, err);
@@ -122,10 +128,61 @@ export function generateStatic(operation: IHttpOperation, source: JSONSchema): E
   );
 }
 
+function promoteUnionExamples(source: JSONSchema): void {
+  const schemaMaps = new Set(['properties', 'patternProperties', 'definitions', '$defs', 'dependentSchemas']);
+  const schemaKeywords = [
+    ...schemaMaps,
+    'additionalProperties',
+    'allOf',
+    'anyOf',
+    'oneOf',
+    'items',
+    'not',
+    'if',
+    'then',
+    'else',
+    'contains',
+    'propertyNames',
+  ];
+  const visited = new WeakSet<object>();
+
+  const visit = (schema: any): void => {
+    if (!schema || typeof schema !== 'object' || visited.has(schema)) return;
+    visited.add(schema);
+
+    // The sampler traverses unions before checking examples on the union schema itself.
+    if (
+      (schema.anyOf?.length || schema.oneOf?.length) &&
+      Array.isArray(schema.examples) &&
+      schema.examples.length > 0 &&
+      schema.example === undefined
+    ) {
+      schema.example = schema.examples[0];
+    }
+
+    for (const keyword of schemaKeywords) {
+      const child = schema[keyword];
+      if (!child || typeof child !== 'object') continue;
+      if (schemaMaps.has(keyword)) {
+        Object.values(child).forEach(visit);
+      } else if (Array.isArray(child)) {
+        child.forEach(visit);
+      } else {
+        visit(child);
+      }
+    }
+  };
+
+  visit(source);
+}
+
 export class GeneratorError extends Error {}
 
 export class SchemaTooComplexGeneratorError extends GeneratorError {
-  constructor(operation: IHttpOperation, public readonly cause: Error) {
+  constructor(
+    operation: IHttpOperation,
+    public readonly cause: Error
+  ) {
     super(
       `The operation ${operation.method.toUpperCase()} ${
         operation.path