diff --git a/packages/openapi/src/openapi-generator-operation.test.ts b/packages/openapi/src/openapi-generator-operation.test.ts
index 96c4c3b99..3a60a25bb 100644
--- a/packages/openapi/src/openapi-generator-operation.test.ts
+++ b/packages/openapi/src/openapi-generator-operation.test.ts
@@ -614,6 +614,55 @@ describe('openAPIGenerator operation builders', () => {
       })
     })
 
+    it.each([
+      {
+        // Effect emits `Schema.Literal(201)` as `{ type: 'number', enum: [201] }`
+        name: 'a single-value enum',
+        status: { type: 'number', enum: [201], description: 'created' },
+        descriptions: { 201: 'created' },
+      },
+      {
+        name: 'a multi-value enum',
+        status: { type: 'number', enum: [200, 201, 200], description: 'success' },
+        descriptions: { 200: 'success', 201: 'success' },
+      },
+      {
+        // zod and valibot emit a union of literals as `anyOf` of `const` schemas
+        name: 'a union of literals',
+        status: {
+          description: 'accepted',
+          anyOf: [
+            { type: 'number', const: 201, description: 'created' },
+            { type: 'number', const: 202 },
+            { type: 'number', enum: [203, 204] },
+          ],
+        },
+        descriptions: { 201: 'created', 202: 'accepted', 203: 'accepted', 204: 'accepted' },
+      },
+    ])('maps $name detailed status to per-status responses', ({ status, descriptions }) => {
+      const { ctx, operation } = createContext()
+
+      buildSuccessResponse(ctx, operation, testDef({
+        outputs: [testSchema({
+          type: 'object',
+          properties: {
+            status: status as any,
+            headers: { type: 'object', properties: { 'x-id': { type: 'string' } }, required: ['x-id'] },
+            body: { type: 'string' },
+          },
+          required: ['status', 'headers', 'body'],
+        })],
+      }), { outputStructure: 'detailed' })
+
+      expect(operation.responses).toEqual(Object.fromEntries(
+        Object.entries(descriptions).map(([code, description]) => [code, {
+          description,
+          headers: { 'x-id': { required: true, schema: { type: 'string' } } },
+          content: { 'application/json': { schema: { type: 'string' } } },
+        }]),
+      ))
+    })
+
     it.each([
       {
         name: 'a detailed output member is not an object',
@@ -626,7 +675,7 @@ describe('openAPIGenerator operation builders', () => {
         message: 'invalid "status" field in the detailed output schema',
       },
       {
-        name: 'a detailed status is not a const integer',
+        name: 'a detailed status is not a literal integer',
         output: { type: 'object', properties: { status: { type: 'number' } }, required: ['status'] },
         message: 'invalid "status" field in the detailed output schema',
       },
@@ -635,6 +684,31 @@ describe('openAPIGenerator operation builders', () => {
         output: { type: 'object', properties: { status: { const: 400 } }, required: ['status'] },
         message: 'invalid "status" field in the detailed output schema',
       },
+      {
+        name: 'a detailed enum status contains a non-success status',
+        output: { type: 'object', properties: { status: { type: 'number', enum: [200, 400] } }, required: ['status'] },
+        message: 'invalid "status" field in the detailed output schema',
+      },
+      {
+        name: 'a detailed enum status is empty',
+        output: { type: 'object', properties: { status: { type: 'number', enum: [] } }, required: ['status'] },
+        message: 'invalid "status" field in the detailed output schema',
+      },
+      {
+        name: 'a detailed status union is empty',
+        output: { type: 'object', properties: { status: { anyOf: [] } }, required: ['status'] },
+        message: 'invalid "status" field in the detailed output schema',
+      },
+      {
+        name: 'a detailed status union contains a non-literal member',
+        output: { type: 'object', properties: { status: { anyOf: [{ const: 200 }, { type: 'number' }] } }, required: ['status'] },
+        message: 'invalid "status" field in the detailed output schema',
+      },
+      {
+        name: 'a detailed status union contains a non-integer literal',
+        output: { type: 'object', properties: { status: { anyOf: [{ const: 200 }, { const: '201' }] } }, required: ['status'] },
+        message: 'invalid "status" field in the detailed output schema',
+      },
     ])('throws when $name', ({ output, message }) => {
       const { ctx, operation } = createContext()
 
diff --git a/packages/openapi/src/openapi-generator-operation.ts b/packages/openapi/src/openapi-generator-operation.ts
index d88095f35..3e925b7e5 100644
--- a/packages/openapi/src/openapi-generator-operation.ts
+++ b/packages/openapi/src/openapi-generator-operation.ts
@@ -410,39 +410,76 @@ function extractDetailedResponseParts(
     }
 
     const statusSchema = entries.find(([name]) => name === 'status')?.[1]
+    const statuses = statusSchema === undefined
+      ? new Map([[defaultStatus, undefined]])
+      : extractDetailedStatuses(statusSchema)
 
-    if (statusSchema !== undefined && (typeof statusSchema !== 'object' || !Number.isInteger(statusSchema.const) || statusSchema.const >= 400)) {
+    if (!statuses) {
       throw new OpenAPIGeneratorError(
         `invalid "status" field in the detailed output schema.\n`
-        + `  Expected: a literal (const) integer below 400\n`
+        + `  Expected: literal integers below 400 (const, enum, or a union of them)\n`
         + `  Received: ${stringifyJSON(statusSchema)}`,
       )
     }
 
-    const status = (statusSchema?.const as number || undefined) ?? defaultStatus
+    const headersSchema = entries.find(([name]) => name === 'headers')?.[1]
+    const bodySchema = entries.find(([name]) => name === 'body')?.[1]
+
+    for (const [status, description] of statuses) {
+      let parts = partsByStatus.get(status)
+      if (!parts) {
+        parts = { descriptions: [], bodies: [], headers: [] }
+        partsByStatus.set(status, parts)
+      }
 
-    let parts = partsByStatus.get(status)
-    if (!parts) {
-      parts = { descriptions: [], bodies: [], headers: [] }
-      partsByStatus.set(status, parts)
+      if (description !== undefined) {
+        parts.descriptions.push(description)
+      }
+
+      if (headersSchema !== undefined) {
+        parts.headers.push(headersSchema)
+      }
+
+      if (bodySchema !== undefined) {
+        parts.bodies.push(bodySchema)
+      }
     }
+  }
+
+  return partsByStatus
+}
 
-    if (statusSchema?.description !== undefined) {
-      parts.descriptions.push(statusSchema.description)
+/**
+ * Collects every status a detailed output `status` schema allows, mapped to its description.
+ * Accepts `const`, `enum` (how Effect, arktype, and valibot `picklist` emit literals), or a union of them.
+ * Returns `undefined` when any member is not a literal integer below 400.
+ */
+function extractDetailedStatuses(schema: JsonSchema): Map<number, string | undefined> | undefined {
+  const statuses = new Map<number, string | undefined>()
+
+  for (const member of flattenJsonUnionSchema(schema)) {
+    if (typeof member !== 'object') {
+      return undefined
     }
 
-    const headersSchema = entries.find(([name]) => name === 'headers')?.[1]
-    if (headersSchema !== undefined) {
-      parts.headers.push(headersSchema)
+    const values = member.const !== undefined ? [member.const] : member.enum
+
+    if (!values?.length) {
+      return undefined
     }
 
-    const bodySchema = entries.find(([name]) => name === 'body')?.[1]
-    if (bodySchema !== undefined) {
-      parts.bodies.push(bodySchema)
+    for (const value of values) {
+      if (!Number.isInteger(value) || value >= 400) {
+        return undefined
+      }
+
+      if (!statuses.has(value)) {
+        statuses.set(value, member.description)
+      }
     }
   }
 
-  return partsByStatus
+  return statuses.size ? statuses : undefined
 }
 
 export function buildErrorResponse(