diff --git a/trustify/client/client.py b/trustify/client/client.py
index e329304d9..782aac1f8 100644
--- a/trustify/client/client.py
+++ b/trustify/client/client.py
@@ -541,7 +541,7 @@ def authenticate():
     # This should be invoked if a payment is necessary
     # This is being tested and will have to be cleaned and organized 
     # once the protocol is finalized.
-    if r.challenge and all_payment_challenge(r):
+    while r.challenge and all_payment_challenge(r):
         # dont need to change domain names here
         paymentChallenges, temp = challenge_factory(r, os.path.abspath(req_file), os.path.abspath(key_file), config)
         for chall in paymentChallenges:
@@ -556,7 +556,7 @@ def authenticate():
         # Send the proceed message
         r = decode(do(upstream, k))
 
-        while r.proceed.IsInitialized() or r.challenge:
+        while r.proceed.IsInitialized():
             if r.proceed.IsInitialized():
                 delay = min(r.proceed.polldelay, 60)
                 logger.debug("waiting %d" % delay)