diff --git a/openapi-codegen/core/src/main/scala/sttp/tapir/codegen/EndpointGenerator.scala b/openapi-codegen/core/src/main/scala/sttp/tapir/codegen/EndpointGenerator.scala
index 5f88c23bc0..7b388ffc93 100644
--- a/openapi-codegen/core/src/main/scala/sttp/tapir/codegen/EndpointGenerator.scala
+++ b/openapi-codegen/core/src/main/scala/sttp/tapir/codegen/EndpointGenerator.scala
@@ -309,35 +309,55 @@ class EndpointGenerator {
     // .errorOut(stringBody)
     // .out(jsonBody[List[Book]])
 
-    responses
-      .map { resp =>
-        val d = s""".description("${JavaEscape.escapeString(resp.description)}")"""
+    val (outs, errorOuts) = responses.partition { resp =>
+      resp.content match {
+        case Nil | _ +: Nil =>
+          resp.code match {
+            case okStatus(_)                => true
+            case "default" | errorStatus(_) => false
+            case x                          => bail(s"Statuscode mapping is incomplete! Cannot handle $x")
+          }
+        case _ => bail("We can handle only one return content!")
+      }
+    }
+    def bodyFmt(resp: OpenapiResponse): String = {
+      val d = s""".description("${JavaEscape.escapeString(resp.description)}")"""
+      resp.content match {
+        case Nil => ""
+        case content +: Nil =>
+          s"${contentTypeMapper(content.contentType, content.schema, streamingImplementation)}$d"
+      }
+    }
+    def mappedGroup(group: Seq[OpenapiResponse]) = group match {
+      case Nil => None
+      case resp +: Nil =>
         resp.content match {
           case Nil =>
+            val d = s""".description("${JavaEscape.escapeString(resp.description)}")"""
             resp.code match {
-              case "200" | "default" => ""
-              case okStatus(s)       => s".out(statusCode(sttp.model.StatusCode($s))$d)"
-              case errorStatus(s)    => s".errorOut(statusCode(sttp.model.StatusCode($s))$d)"
-            }
-          case content +: Nil =>
-            resp.code match {
-              case "200" =>
-                s".out(${contentTypeMapper(content.contentType, content.schema, streamingImplementation)}$d)"
-              case okStatus(s) =>
-                s".out(${contentTypeMapper(content.contentType, content.schema, streamingImplementation)}$d.and(statusCode(sttp.model.StatusCode($s))))"
-              case "default" =>
-                s".errorOut(${contentTypeMapper(content.contentType, content.schema, streamingImplementation)}$d)"
-              case errorStatus(s) =>
-                s".errorOut(${contentTypeMapper(content.contentType, content.schema, streamingImplementation)}$d.and(statusCode(sttp.model.StatusCode($s))))"
-              case x =>
-                bail(s"Statuscode mapping is incomplete! Cannot handle $x")
+              case "200" | "default" => None
+              case okStatus(s)       => Some(s"statusCode(sttp.model.StatusCode($s))$d")
+              case errorStatus(s)    => Some(s"statusCode(sttp.model.StatusCode($s))$d")
             }
-          case _ => bail("We can handle only one return content!")
+          case _ =>
+            Some(resp.code match {
+              case "200" | "default" => s"${bodyFmt(resp)}"
+              case okStatus(s)       => s"${bodyFmt(resp)}.and(statusCode(sttp.model.StatusCode($s)))"
+              case errorStatus(s)    => s"${bodyFmt(resp)}.and(statusCode(sttp.model.StatusCode($s)))"
+            })
         }
-      }
-      .sorted
-      .filter(_.nonEmpty)
-      .mkString("\n")
+      case many =>
+        if (many.map(_.code).distinct.size != many.size) bail("Cannot construct schema for multiple responses with same status code")
+        val oneOfs = many.map { m =>
+          val code = if (m.code == "default") "400" else m.code
+          s"oneOfVariant(sttp.model.StatusCode(${code}), ${bodyFmt(m)})"
+        }
+        Some(s"oneOf(${oneOfs.mkString(", ")})")
+    }
+    val mappedOuts = mappedGroup(outs).map(s => s".out($s)")
+    val mappedErrorOuts = mappedGroup(errorOuts).map(s => s".errorOut($s)")
+
+    Seq(mappedErrorOuts, mappedOuts).flatten.mkString("\n")
   }
 
   private def contentTypeMapper(
diff --git a/openapi-codegen/core/src/main/scala/sttp/tapir/codegen/SchemaGenerator.scala b/openapi-codegen/core/src/main/scala/sttp/tapir/codegen/SchemaGenerator.scala
index cf9b2582ac..7d6bc95434 100644
--- a/openapi-codegen/core/src/main/scala/sttp/tapir/codegen/SchemaGenerator.scala
+++ b/openapi-codegen/core/src/main/scala/sttp/tapir/codegen/SchemaGenerator.scala
@@ -54,7 +54,10 @@ object SchemaGenerator {
             false
           ) -> "implicit lazy val anyTapirSchema: sttp.tapir.Schema[io.circe.Json] = sttp.tapir.Schema.any[io.circe.Json]"
         )
-      else throw new NotImplementedError("any not implemented for json libs other than circe")
+      else
+        throw new NotImplementedError(
+          s"any not implemented for json libs other than circe (problematic models: ${schemasWithAny.map(_._1)})"
+        )
     val openApiSchemasWithTapirSchemas = doc.components
       .map(_.schemas.map {
         case (name, _: OpenapiSchemaEnum) =>
diff --git a/openapi-codegen/core/src/test/scala/sttp/tapir/codegen/TestHelpers.scala b/openapi-codegen/core/src/test/scala/sttp/tapir/codegen/TestHelpers.scala
index 34094f11dd..b07beca85c 100644
--- a/openapi-codegen/core/src/test/scala/sttp/tapir/codegen/TestHelpers.scala
+++ b/openapi-codegen/core/src/test/scala/sttp/tapir/codegen/TestHelpers.scala
@@ -100,6 +100,12 @@ object TestHelpers {
       |                type: array
       |                items:
       |                  $ref: '#/components/schemas/Book'
+      |        '401':
+      |          description: 'unauthorized'
+      |          content:
+      |            text/plain:
+      |              schema:
+      |                type: string
       |        default:
       |          description: ''
       |          content:
@@ -165,6 +171,7 @@ object TestHelpers {
                 "",
                 Seq(OpenapiResponseContent("application/json", OpenapiSchemaArray(OpenapiSchemaRef("#/components/schemas/Book"), false)))
               ),
+              OpenapiResponse("401", "unauthorized", Seq(OpenapiResponseContent("text/plain", OpenapiSchemaString(false)))),
               OpenapiResponse("default", "", Seq(OpenapiResponseContent("text/plain", OpenapiSchemaString(false))))
             ),
             requestBody = None,