diff --git a/.changeset/openapi-nullable-recursion.md b/.changeset/openapi-nullable-recursion.md
new file mode 100644
index 000000000..367166228
--- /dev/null
+++ b/.changeset/openapi-nullable-recursion.md
@@ -0,0 +1,6 @@
+---
+"@gitbook/react-openapi": patch
+"gitbook": patch
+---
+
+Fix OpenAPI schemas that reference themselves through a nullable union rendering forever when expanded, which crashed PDF exports.
diff --git a/packages/react-openapi/src/OpenAPISchemaServer.test.tsx b/packages/react-openapi/src/OpenAPISchemaServer.test.tsx
new file mode 100644
index 000000000..fbe85c8e9
--- /dev/null
+++ b/packages/react-openapi/src/OpenAPISchemaServer.test.tsx
@@ -0,0 +1,69 @@
+import { describe, expect, it } from 'bun:test';
+import { renderToReadableStream } from 'react-dom/server';
+
+import { parseOpenAPI } from '@gitbook/openapi-parser';
+
+import type { OpenAPIClientContext } from './context';
+import { OpenAPIRootSchema } from './OpenAPISchemaServer';
+import { resolveOpenAPISchemas } from './schemas/resolveOpenAPISchemas';
+import { translations } from './translations';
+
+const context: OpenAPIClientContext = {
+    translation: translations.en,
+    icons: {
+        chevronDown: null,
+        chevronRight: null,
+        plus: null,
+        copy: null,
+        check: null,
+        lock: null,
+        mcp: null,
+        hashtag: null,
+    },
+    expandAllModelSections: true,
+    scalarRuntimeURL: '',
+    $$isClientContext$$: true,
+};
+
+describe('OpenAPIRootSchema', () => {
+    it('should stop at a self-reference behind a nullable union when expanded', async () => {
+        const { filesystem } = await parseOpenAPI({
+            value: JSON.stringify({
+                openapi: '3.1.0',
+                info: { title: 'Test', version: '1.0.0' },
+                paths: {},
+                components: {
+                    schemas: {
+                        FilterClause: {
+                            type: 'object',
+                            properties: {
+                                AND: {
+                                    anyOf: [
+                                        {
+                                            type: 'array',
+                                            items: { $ref: '#/components/schemas/FilterClause' },
+                                        },
+                                        { type: 'null' },
+                                    ],
+                                },
+                            },
+                        },
+                    },
+                },
+            }),
+            rootURL: 'memory://spec.json',
+        });
+        const resolved = await resolveOpenAPISchemas(filesystem, { schemas: ['FilterClause'] });
+        const schema = resolved?.schemas[0]?.schema;
+        if (!schema) {
+            throw new Error('FilterClause not resolved');
+        }
+
+        const stream = await renderToReadableStream(
+            <OpenAPIRootSchema schema={schema} context={context} />
+        );
+        const html = await new Response(stream).text();
+
+        expect(html).toContain('AND');
+    });
+});
diff --git a/packages/react-openapi/src/utils.test.ts b/packages/react-openapi/src/utils.test.ts
index 6c9722d48..8345f9f72 100644
--- a/packages/react-openapi/src/utils.test.ts
+++ b/packages/react-openapi/src/utils.test.ts
@@ -190,6 +190,14 @@ describe('extractNonNullTypes', () => {
 });
 
 describe('normalizeNullableUnion', () => {
+    it('should return the same object for the same input', () => {
+        const schema: OpenAPIV3_1.SchemaObject = {
+            anyOf: [{ type: 'array', items: { type: 'string' } }, { type: 'null' }],
+        };
+
+        expect(normalizeNullableUnion(schema)).toBe(normalizeNullableUnion(schema));
+    });
+
     it('should collapse anyOf with a single non-null member into a nullable schema', () => {
         const schema: OpenAPIV3_1.SchemaObject = {
             anyOf: [{ type: 'string' }, { type: 'null' }],
diff --git a/packages/react-openapi/src/utils.ts b/packages/react-openapi/src/utils.ts
index b8d67ad4b..2f130c9b8 100644
--- a/packages/react-openapi/src/utils.ts
+++ b/packages/react-openapi/src/utils.ts
@@ -287,6 +287,10 @@ function isNullSchema(schema: OpenAPIV3.SchemaObject | OpenAPIV3.ReferenceObject
     return type === 'null';
 }
 
+// Circular-ref tracking compares schemas by identity: a fresh copy on every render lets a
+// self-referencing nullable property (`anyOf: [{ items: Self }, null]`) recurse forever when expanded.
+const normalizedNullableUnions = new WeakMap<OpenAPIV3.SchemaObject, OpenAPIV3.SchemaObject>();
+
 /**
  * Normalize the OpenAPI 3.1+ idiom of expressing nullability through `anyOf`/`oneOf`
  * (e.g. `anyOf: [{ type: 'string' }, { type: 'null' }]`) into a regular nullable schema,
@@ -301,7 +305,17 @@ export function normalizeNullableUnion(
     schema: OpenAPIV3.SchemaObject | OpenAPIV3_1.SchemaObject
 ): OpenAPIV3.SchemaObject {
     const typed = schema as OpenAPIV3.SchemaObject;
+    const cached = normalizedNullableUnions.get(typed);
+    if (cached) {
+        return cached;
+    }
 
+    const normalized = normalizeNullableUnionUncached(typed);
+    normalizedNullableUnions.set(typed, normalized);
+    return normalized;
+}
+
+function normalizeNullableUnionUncached(typed: OpenAPIV3.SchemaObject): OpenAPIV3.SchemaObject {
     const isAnyOf = Array.isArray(typed.anyOf);
     const isOneOf = !isAnyOf && Array.isArray(typed.oneOf);
     if (!isAnyOf && !isOneOf) {