diff --git a/Arduino.mk b/Arduino.mk
index c83ad0d..0b4ed61 100644
--- a/Arduino.mk
+++ b/Arduino.mk
@@ -744,13 +744,23 @@ ifndef RESET_CMD
 	endif
     ifneq ($(CATERINA),)
         ifneq (,$(findstring CYGWIN,$(shell uname -s)))
+          # confirm user is using default cygwin unix Python (which uses ttySx) and not Windows Python (which uses COMx)
+          ifeq ($(shell which python),/usr/bin/python)
             RESET_CMD = $(ARD_RESET_ARDUINO) --caterina $(ARD_RESET_OPTS) $(DEVICE_PATH)
+          else
+            RESET_CMD = $(ARD_RESET_ARDUINO) --caterina $(ARD_RESET_OPTS) $(call get_monitor_port)
+          endif
         else
             RESET_CMD = $(ARD_RESET_ARDUINO) --caterina $(ARD_RESET_OPTS) $(call get_monitor_port)
         endif
     else
         ifneq (,$(findstring CYGWIN,$(shell uname -s)))
+          # confirm user is using default cygwin unix Python (which uses ttySx) and not Windows Python (which uses COMx)
+          ifeq ($(shell which python),/usr/bin/python)
             RESET_CMD = $(ARD_RESET_ARDUINO) $(ARD_RESET_OPTS) $(DEVICE_PATH)
+          else
+            RESET_CMD = $(ARD_RESET_ARDUINO) $(ARD_RESET_OPTS) $(call get_monitor_port)
+          endif
         else
             RESET_CMD = $(ARD_RESET_ARDUINO) $(ARD_RESET_OPTS) $(call get_monitor_port)
         endif