diff --git a/plugins/out_cloudwatch_logs/cloudwatch_api.c b/plugins/out_cloudwatch_logs/cloudwatch_api.c
index 56e91e6d557..3bdf6443ca4 100644
--- a/plugins/out_cloudwatch_logs/cloudwatch_api.c
+++ b/plugins/out_cloudwatch_logs/cloudwatch_api.c
@@ -50,6 +50,8 @@
 
 #define ERR_CODE_ALREADY_EXISTS         "ResourceAlreadyExistsException"
 #define ERR_CODE_INVALID_SEQUENCE_TOKEN "InvalidSequenceTokenException"
+#define ERR_CODE_NOT_FOUND              "ResourceNotFoundException"
+
 
 #define AMZN_REQUEST_ID_HEADER          "x-amzn-RequestId"
 
@@ -1040,7 +1042,7 @@ struct log_stream *get_dynamic_log_stream(struct flb_cloudwatch *ctx,
     }
     new_stream->name = name;
 
-    ret = create_log_stream(ctx, new_stream);
+    ret = create_log_stream(ctx, new_stream, FLB_TRUE);
     if (ret < 0) {
         log_stream_destroy(new_stream);
         return NULL;
@@ -1060,7 +1062,7 @@ struct log_stream *get_log_stream(struct flb_cloudwatch *ctx,
     if (ctx->log_stream_name) {
         stream = &ctx->stream;
         if (ctx->stream_created == FLB_FALSE) {
-            ret = create_log_stream(ctx, stream);
+            ret = create_log_stream(ctx, stream, FLB_TRUE);
             if (ret < 0) {
                 return NULL;
             }
@@ -1234,7 +1236,8 @@ int create_log_group(struct flb_cloudwatch *ctx)
     return -1;
 }
 
-int create_log_stream(struct flb_cloudwatch *ctx, struct log_stream *stream)
+int create_log_stream(struct flb_cloudwatch *ctx, struct log_stream *stream,
+                      int can_retry)
 {
 
     struct flb_http_client *c = NULL;
@@ -1242,6 +1245,7 @@ int create_log_stream(struct flb_cloudwatch *ctx, struct log_stream *stream)
     flb_sds_t body;
     flb_sds_t tmp;
     flb_sds_t error;
+    int ret;
 
     flb_plg_info(ctx->ins, "Creating log stream %s in log group %s",
                  stream->name, ctx->log_group);
@@ -1300,6 +1304,33 @@ int create_log_stream(struct flb_cloudwatch *ctx, struct log_stream *stream)
                     flb_http_client_destroy(c);
                     return 0;
                 }
+
+                if (strcmp(error, ERR_CODE_NOT_FOUND) == 0) {
+                    flb_sds_destroy(body);
+                    flb_sds_destroy(error);
+                    flb_http_client_destroy(c);
+
+                    if (ctx->create_group == FLB_TRUE) {
+                        flb_plg_info(ctx->ins, "Log Group %s not found. Will attempt to create it.",
+                                 ctx->log_group);
+                        ret = create_log_group(ctx);
+                        if (ret < 0) {
+                            return -1;
+                        } else {
+                            if (can_retry == FLB_TRUE) {
+                                /* retry stream creation */
+                                return create_log_stream(ctx, stream, FLB_FALSE);
+                            } else {
+                                /* we failed to create the stream */
+                                return -1;
+                            }
+                        }
+                    } else {
+                        flb_plg_error(ctx->ins, "Log Group %s not found and `auto_create_group` disabled.",
+                                     ctx->log_group);
+                    }
+                    return -1;
+                }
                 /* some other error occurred; notify user */
                 flb_aws_print_error(c->resp.payload, c->resp.payload_size,
                                     "CreateLogStream", ctx->ins);
diff --git a/plugins/out_cloudwatch_logs/cloudwatch_api.h b/plugins/out_cloudwatch_logs/cloudwatch_api.h
index 452b01e59ba..128c15007a1 100644
--- a/plugins/out_cloudwatch_logs/cloudwatch_api.h
+++ b/plugins/out_cloudwatch_logs/cloudwatch_api.h
@@ -45,7 +45,7 @@ void cw_flush_destroy(struct cw_flush *buf);
 int process_and_send(struct flb_cloudwatch *ctx, const char *input_plugin, struct cw_flush *buf,
                      struct log_stream *stream,
                      const char *data, size_t bytes);
-int create_log_stream(struct flb_cloudwatch *ctx, struct log_stream *stream);
+int create_log_stream(struct flb_cloudwatch *ctx, struct log_stream *stream, int can_retry);
 struct log_stream *get_log_stream(struct flb_cloudwatch *ctx,
                                   const char *tag, int tag_len);
 int put_log_events(struct flb_cloudwatch *ctx, struct cw_flush *buf,
diff --git a/plugins/out_cloudwatch_logs/cloudwatch_logs.c b/plugins/out_cloudwatch_logs/cloudwatch_logs.c
index 2f31e99888e..1b9ee282f49 100644
--- a/plugins/out_cloudwatch_logs/cloudwatch_logs.c
+++ b/plugins/out_cloudwatch_logs/cloudwatch_logs.c
@@ -382,7 +382,6 @@ static void cb_cloudwatch_flush(struct flb_event_chunk *event_chunk,
                                 struct flb_config *config)
 {
     struct flb_cloudwatch *ctx = out_context;
-    int ret;
     int event_count;
     struct log_stream *stream = NULL;
     (void) i_ins;
@@ -390,13 +389,6 @@ static void cb_cloudwatch_flush(struct flb_event_chunk *event_chunk,
 
     ctx->buf->put_events_calls = 0;
 
-    if (ctx->create_group == FLB_TRUE && ctx->group_created == FLB_FALSE) {
-        ret = create_log_group(ctx);
-        if (ret < 0) {
-            FLB_OUTPUT_RETURN(FLB_RETRY);
-        }
-    }
-
     stream = get_log_stream(ctx,
                             event_chunk->tag, flb_sds_len(event_chunk->tag));
     if (!stream) {