diff --git a/tools/macosx/maple_upload b/tools/macosx/maple_upload
index 3521aa1ef..2ffec6cc4 100755
--- a/tools/macosx/maple_upload
+++ b/tools/macosx/maple_upload
@@ -52,6 +52,14 @@ fi
 
 ${DFU_UTIL} -d ${usbID} -a ${altID} -D ${binfile} -R ${dfuse_addr} -R
 
+# DFU_UTIL doesn't reset properly in new Mac OS, use reenumerate tool from Prober.app
+if (system_profiler SPUSBDataType | grep --quiet Maple\ 003) then
+    echo Maple 003 bootloader found, try to reenumerate it.
+    ${DIR}/reenumerate -v 0x1eaf,0x0003
+else
+    echo Maple 003 bootloader not found 
+fi
+
 echo -n Waiting for ${dummy_port_fullpath} serial...
 
 COUNTER=0
diff --git a/tools/macosx/reenumerate b/tools/macosx/reenumerate
new file mode 100755
index 000000000..9e9275d8b
Binary files /dev/null and b/tools/macosx/reenumerate differ