diff --git a/.changeset/tasty-knives-matter.md b/.changeset/tasty-knives-matter.md
new file mode 100644
index 000000000..4efe9c01c
--- /dev/null
+++ b/.changeset/tasty-knives-matter.md
@@ -0,0 +1,5 @@
+---
+"openapi-typescript": patch
+---
+
+Fall back to TypeScript unions for long oneOf lists
diff --git a/packages/openapi-typescript/src/utils.ts b/packages/openapi-typescript/src/utils.ts
index 9061d7b7c..e0dc0455b 100644
--- a/packages/openapi-typescript/src/utils.ts
+++ b/packages/openapi-typescript/src/utils.ts
@@ -180,9 +180,17 @@ export function tsNonNullable(type: string): string {
   return `NonNullable<${type}>`;
 }
 
-/** OneOf<T> (custom) */
+/**
+ * OneOf<T>
+ * TypeScript unions are not exclusive @see https://stackoverflow.com/questions/42123407/does-typescript-support-mutually-exclusive-types
+ * However, at a certain size, the helper type becomes too complex for inference to work. Hence the > check.
+ */
 export function tsOneOf(...types: string[]): string {
-  if (types.length === 1) return types[0];
+  if (types.length === 1) {
+    return types[0];
+  } else if (types.length > 5) {
+    return tsUnionOf(...types);
+  }
   return `OneOf<[${types.join(", ")}]>`;
 }
 
diff --git a/packages/openapi-typescript/test/schema-object.test.ts b/packages/openapi-typescript/test/schema-object.test.ts
index cd6b2cdf1..7f292d561 100644
--- a/packages/openapi-typescript/test/schema-object.test.ts
+++ b/packages/openapi-typescript/test/schema-object.test.ts
@@ -335,6 +335,36 @@ describe("Schema Object", () => {
 }]>`);
       });
 
+      test("falls back to union at high complexity", () => {
+        const schema: SchemaObject = {
+          oneOf: [
+            { type: "object", properties: { string: { type: "string" } }, required: ["string"] },
+            { type: "object", properties: { boolean: { type: "boolean" } }, required: ["boolean"] },
+            { type: "object", properties: { number: { type: "number" } }, required: ["number"] },
+            { type: "object", properties: { array: { type: "array", items: { type: "string" } } }, required: ["array"] },
+            { type: "object", properties: { object: { type: "object", properties: { string: { type: "string" } }, required: ["string"] } }, required: ["object"] },
+            { type: "object", properties: { enum: { type: "string", enum: ["foo", "bar", "baz"] } }, required: ["enum"] },
+          ],
+        };
+        const generated = transformSchemaObject(schema, options);
+        expect(generated).toBe(`{
+  string: string;
+} | {
+  boolean: boolean;
+} | {
+  number: number;
+} | {
+  array: (string)[];
+} | {
+  object: {
+    string: string;
+  };
+} | ({
+  /** @enum {string} */
+  enum: "foo" | "bar" | "baz";
+})`);
+      });
+
       test("discriminator", () => {
         const schema: SchemaObject = {
           type: "object",