diff --git a/rowers/middleware.py b/rowers/middleware.py
index c1b968f2..3b58f0c8 100644
--- a/rowers/middleware.py
+++ b/rowers/middleware.py
@@ -136,6 +136,12 @@ class RowerPlanMiddleWare(object):
                                                          paymentprocessor='braintree')
                     r.paidplan = basicplans[0]
                     r.save()
+                    # remove from Free Coach groups
+                    for group in r.coachinggroups.all():
+                        coach = rower.objects.get(mycoachgroup=group)
+                        if coach.rowerplan == 'freecoach':
+                            r.coachinggroups.remove(group)
+                    
                     # send email
                     job = myqueue(queue,
                                   handle_sendemail_expired,
diff --git a/rowers/models.py b/rowers/models.py
index ec2f772e..f9d2ae9f 100644
--- a/rowers/models.py
+++ b/rowers/models.py
@@ -878,7 +878,17 @@ class Rower(models.Model):
     def clean_email(self):
         return self.user.email.lower()
 
-
+    def save(self, *args, **kwargs):
+        try:
+            for group in self.coachinggroups.all():
+                coach = Rower.objects.get(mycoachgroup=group)
+                if coach.rowerplan == 'freecoach':
+                    self.coachinggroups.remove(group)
+        except ValueError:
+            pass
+        
+        super(Rower, self).save(*args, **kwargs)
+    
 class DeactivateUserForm(forms.ModelForm):
     class Meta:
         model = User
diff --git a/rowers/tests/testdata/testdata.csv.gz b/rowers/tests/testdata/testdata.csv.gz
index 4f7fc75a..9941ccb4 100644
Binary files a/rowers/tests/testdata/testdata.csv.gz and b/rowers/tests/testdata/testdata.csv.gz differ