diff --git a/src/bitmessageqt/__init__.py b/src/bitmessageqt/__init__.py
index ce3f0eff..df6b3b45 100644
--- a/src/bitmessageqt/__init__.py
+++ b/src/bitmessageqt/__init__.py
@@ -2347,12 +2347,31 @@ class MyForm(QtGui.QMainWindow):
             if float(self.settingsDialogInstance.ui.lineEditSmallMessageDifficulty.text()) >= 1:
                 shared.config.set('bitmessagesettings', 'defaultpayloadlengthextrabytes', str(int(float(
                     self.settingsDialogInstance.ui.lineEditSmallMessageDifficulty.text()) * shared.networkDefaultPayloadLengthExtraBytes)))
+
+            acceptableDifficultyChanged = False
+            
             if float(self.settingsDialogInstance.ui.lineEditMaxAcceptableTotalDifficulty.text()) >= 1 or float(self.settingsDialogInstance.ui.lineEditMaxAcceptableTotalDifficulty.text()) == 0:
-                shared.config.set('bitmessagesettings', 'maxacceptablenoncetrialsperbyte', str(int(float(
-                    self.settingsDialogInstance.ui.lineEditMaxAcceptableTotalDifficulty.text()) * shared.networkDefaultProofOfWorkNonceTrialsPerByte)))
+                if shared.config.get('bitmessagesettings','maxacceptablenoncetrialsperbyte') != str(int(float(
+                    self.settingsDialogInstance.ui.lineEditMaxAcceptableTotalDifficulty.text()) * shared.networkDefaultProofOfWorkNonceTrialsPerByte)):
+                    # the user changed the max acceptable total difficulty
+                    acceptableDifficultyChanged = True
+                    shared.config.set('bitmessagesettings', 'maxacceptablenoncetrialsperbyte', str(int(float(
+                        self.settingsDialogInstance.ui.lineEditMaxAcceptableTotalDifficulty.text()) * shared.networkDefaultProofOfWorkNonceTrialsPerByte)))
             if float(self.settingsDialogInstance.ui.lineEditMaxAcceptableSmallMessageDifficulty.text()) >= 1 or float(self.settingsDialogInstance.ui.lineEditMaxAcceptableSmallMessageDifficulty.text()) == 0:
-                shared.config.set('bitmessagesettings', 'maxacceptablepayloadlengthextrabytes', str(int(float(
-                    self.settingsDialogInstance.ui.lineEditMaxAcceptableSmallMessageDifficulty.text()) * shared.networkDefaultPayloadLengthExtraBytes)))
+                if shared.config.get('bitmessagesettings','maxacceptablepayloadlengthextrabytes') != str(int(float(
+                    self.settingsDialogInstance.ui.lineEditMaxAcceptableSmallMessageDifficulty.text()) * shared.networkDefaultPayloadLengthExtraBytes)):
+                    # the user changed the max acceptable small message difficulty
+                    acceptableDifficultyChanged = True
+                    shared.config.set('bitmessagesettings', 'maxacceptablepayloadlengthextrabytes', str(int(float(
+                        self.settingsDialogInstance.ui.lineEditMaxAcceptableSmallMessageDifficulty.text()) * shared.networkDefaultPayloadLengthExtraBytes)))
+            if acceptableDifficultyChanged:
+                # It might now be possible to send msgs which were previously marked as toodifficult. 
+                # Let us change them to 'msgqueued'. The singleWorker will try to send them and will again
+                # mark them as toodifficult if the receiver's required difficulty is still higher than
+                # we are willing to do.
+                sqlExecute('''UPDATE sent SET status='msgqueued' WHERE status='toodifficult' ''')
+                shared.workerQueue.put(('sendmessage', ''))
+            
             #start:UI setting to stop trying to send messages after X days/months
             # I'm open to changing this UI to something else if someone has a better idea.
             if ((self.settingsDialogInstance.ui.lineEditDays.text()=='') and (self.settingsDialogInstance.ui.lineEditMonths.text()=='')):#We need to handle this special case. Bitmessage has its default behavior. The input is blank/blank
diff --git a/src/class_singleWorker.py b/src/class_singleWorker.py
index c238f136..8fad2ea8 100644
--- a/src/class_singleWorker.py
+++ b/src/class_singleWorker.py
@@ -515,14 +515,9 @@ class singleWorker(threading.Thread):
     def sendMsg(self):
         while True: # while we have a msg that needs some work
             
-            # Select just one msg that needs work. We'll get a msg 
-            # which is ready to be sent or a msg which we have sent in 
-            # the last 28 days which were previously marked
-            # as 'toodifficult'. If the user has raised the maximum acceptable
-            # difficulty then those msgs may now be sendable.
+            # Select just one msg that needs work.
             queryreturn = sqlQuery(
-                '''SELECT toaddress, toripe, fromaddress, subject, message, ackdata, status FROM sent WHERE (status='msgqueued' or status='doingmsgpow' or status='forcepow' or (status='toodifficult' and lastactiontime>?)) and folder='sent' LIMIT 1''',
-                int(time.time()) - 2419200)
+                '''SELECT toaddress, toripe, fromaddress, subject, message, ackdata, status FROM sent WHERE (status='msgqueued' or status='doingmsgpow' or status='forcepow') and folder='sent' LIMIT 1''')
             if len(queryreturn) == 0: # if there is no work to do then 
                 break                 # break out of this sendMsg loop and 
                                       # wait for something to get put in the shared.workerQueue.
@@ -717,7 +712,7 @@ class singleWorker(threading.Thread):
                             sqlExecute(
                                 '''UPDATE sent SET status='toodifficult' WHERE ackdata=? ''',
                                 ackdata)
-                            shared.UISignalQueue.put(('updateSentItemStatusByAckdata', (ackdata, tr.translateText("MainWindow", "Problem: The work demanded by the recipient (%1 and %2) is more difficult than you are willing to do.").arg(str(float(requiredAverageProofOfWorkNonceTrialsPerByte) / shared.networkDefaultProofOfWorkNonceTrialsPerByte)).arg(str(float(
+                            shared.UISignalQueue.put(('updateSentItemStatusByAckdata', (ackdata, tr.translateText("MainWindow", "Problem: The work demanded by the recipient (%1 and %2) is more difficult than you are willing to do. %3").arg(str(float(requiredAverageProofOfWorkNonceTrialsPerByte) / shared.networkDefaultProofOfWorkNonceTrialsPerByte)).arg(str(float(
                                 requiredPayloadLengthExtraBytes) / shared.networkDefaultPayloadLengthExtraBytes)).arg(l10n.formatTimestamp()))))
                             continue
             else: # if we are sending a message to ourselves or a chan..