diff --git a/protocol/connections/tokenboardclientapp.go b/protocol/connections/tokenboardclientapp.go
index df85e2b..36e120a 100644
--- a/protocol/connections/tokenboardclientapp.go
+++ b/protocol/connections/tokenboardclientapp.go
@@ -71,7 +71,7 @@ func (ta *TokenBoardClient) Init(connection tapir.Connection) {
 		log.Debugf("Successfully Initialized Connection")
 		go ta.Listen()
 		// Optimistically acquire many tokens for this server...
-		ta.MakePayment()
+		go ta.MakePayment()
 		ta.Replay()
 	} else {
 		connection.Close()
@@ -181,25 +181,29 @@ func (ta *TokenBoardClient) MakePayment() error {
 
 	log.Debugf("Waiting for successful PoW Auth...")
 
-	connected, err := client.Connect(ta.tokenServiceOnion, powTokenApp)
-	if connected == true && err == nil {
-		conn, err := client.WaitForCapabilityOrClose(ta.tokenServiceOnion, applications.HasTokensCapability)
-		if err == nil {
-			powtapp := conn.App().(*applications.TokenApplication)
-			if powtapp != nil {
-				// Update tokens...we need a lock here to prevent SpendToken from modifying the tokens
-				// during this process..
-				log.Debugf("Transcript: %v", powtapp.Transcript().OutputTranscriptToAudit())
-				conn.Close()
-				log.Debugf("Updating Tokens")
-				ta.tokenLock.Lock()
-				ta.tokens = append(ta.tokens, powtapp.Tokens...)
-				if len(ta.tokens) < 5 {
-					go ta.MakePayment()
-				}
-				ta.tokenLock.Unlock()
-				return nil
-			}
+	// We can't have duplicate outbounds...
+	conn, _ := client.GetConnection(ta.tokenServiceOnion)
+	for {
+		if conn == nil {
+			break
+		}
+		conn, _ = client.GetConnection(ta.tokenServiceOnion)
+	}
+
+	client.Connect(ta.tokenServiceOnion, powTokenApp)
+	conn, err := client.WaitForCapabilityOrClose(ta.tokenServiceOnion, applications.HasTokensCapability)
+	if err == nil {
+		powtapp, ok := conn.App().(*applications.TokenApplication)
+		if ok {
+			// Update tokens...we need a lock here to prevent SpendToken from modifying the tokens
+			// during this process..
+			log.Debugf("Updating Tokens")
+			ta.tokenLock.Lock()
+			ta.tokens = append(ta.tokens, powtapp.Tokens...)
+			ta.tokenLock.Unlock()
+			log.Debugf("Transcript: %v", powtapp.Transcript().OutputTranscriptToAudit())
+			conn.Close()
+			return nil
 		}
 	}
 	log.Debugf("Error making payment: to %v %v", ta.tokenServiceOnion, err)