diff --git a/core/contact.go b/core/contact.go
index f5233e4..8cdbc14 100644
--- a/core/contact.go
+++ b/core/contact.go
@@ -5,6 +5,7 @@ import (
 	"github.com/ricochet-im/ricochet-go/core/utils"
 	"github.com/ricochet-im/ricochet-go/rpc"
 	protocol "github.com/s-rah/go-ricochet"
+	channels "github.com/s-rah/go-ricochet/channels"
 	connection "github.com/s-rah/go-ricochet/connection"
 	"golang.org/x/net/context"
 	"log"
@@ -376,8 +377,6 @@ func (c *Contact) connectOutbound(ctx context.Context, connChannel chan *connect
 			continue
 		}
 
-		// XXX-protocol Also move the "this is an outbound request" logic here to kill the silly flag and
-		//     move those out of a scary mutexed path? XXX
 		if !known && !isRequest {
 			log.Printf("Outbound connection to contact says we are not a known contact for %v", c)
 			// XXX Should move to rejected status, stop attempting connections.
@@ -389,6 +388,21 @@ func (c *Contact) connectOutbound(ctx context.Context, connChannel chan *connect
 		} else if known && isRequest {
 			log.Printf("Contact request implicitly accepted for outbound connection by contact %v", c)
 			c.UpdateContactRequest("Accepted")
+			isRequest = false
+		}
+
+		if isRequest {
+			// Need to send a contact request; this will block until the peer accepts or rejects,
+			// the connection fails, or the context is cancelled (which also closes the connection).
+			if err := c.sendContactRequest(oc, ctx); err != nil {
+				log.Printf("Outbound contact request connection closed: %s", err)
+				if err := connector.Backoff(ctx); err != nil {
+					return
+				}
+				continue
+			} else {
+				log.Printf("Outbound contact request accepted, assigning connection")
+			}
 		}
 
 		log.Printf("Assigning outbound connection to contact")
@@ -397,6 +411,77 @@ func (c *Contact) connectOutbound(ctx context.Context, connChannel chan *connect
 	}
 }
 
+type requestChannelHandler struct {
+	Response chan string
+}
+
+func (r *requestChannelHandler) ContactRequest(name, message string) string {
+	log.Printf("BUG: inbound ContactRequest handler called for outbound channel")
+	return "Error"
+}
+func (r *requestChannelHandler) ContactRequestRejected() { r.Response <- "Rejected" }
+func (r *requestChannelHandler) ContactRequestAccepted() { r.Response <- "Accepted" }
+func (r *requestChannelHandler) ContactRequestError()    { r.Response <- "Error" }
+
+// sendContactRequest synchronously delivers a contact request to an authenticated
+// outbound connection and waits for a final (yes/no) reply. This may be cancelled
+// by closing the connection. Once a reply is received, it's passed to
+// UpdateContactRequest to update the status and this function will return. nil is
+// returned for an accepted request when the connection is still established. In all
+// other cases, an error is returned and the connection will be closed.
+func (c *Contact) sendContactRequest(conn *connection.Connection, ctx context.Context) error {
+	log.Printf("Sending request to outbound contact %v", c)
+	ach := &connection.AutoConnectionHandler{}
+	ach.Init()
+
+	processChan := make(chan error)
+	responseChan := make(chan string)
+
+	// No timeouts on outbound contact request; wait forever for a final reply
+	go func() {
+		processChan <- conn.Process(ach)
+	}()
+
+	err := conn.Do(func() error {
+		_, err := conn.RequestOpenChannel("im.ricochet.contact.request",
+			&channels.ContactRequestChannel{
+				Handler: &requestChannelHandler{Response: responseChan},
+				Name:    c.data.Request.MyNickname, // XXX mutex
+				Message: c.data.Request.Message,
+			})
+		return err
+	})
+	if err != nil {
+		// Close and end Process, resulting in an error to processChan and return when done
+		conn.Conn.Close()
+		return <-processChan
+	}
+
+	select {
+	case err := <-processChan:
+		// Should not get nil (via Break) return values here; prevent them
+		if err == nil {
+			closeUnhandledConnection(conn)
+			err = fmt.Errorf("unknown connection break")
+		}
+		return err
+
+	case response := <-responseChan:
+		c.UpdateContactRequest(response)
+		if response == "Accepted" {
+			conn.Break()
+			return <-processChan // nil if connection is still alive
+		} else {
+			conn.Conn.Close()
+			return <-processChan
+		}
+
+	case <-ctx.Done():
+		conn.Conn.Close()
+		return <-processChan
+	}
+}
+
 // considerUsingConnection takes a newly established connection and decides whether
 // the new connection is valid and acceptable, and whether to replace or keep an
 // existing connection. To handle race cases when peers are connecting to eachother,
@@ -454,20 +539,11 @@ func (c *Contact) considerUsingConnection(conn *connection.Connection) error {
 // Assumes c.mutex is held.
 func (c *Contact) onConnectionStateChanged() {
 	if c.connection != nil {
-		if c.data.Request.Pending {
-			if !c.connection.IsInbound {
-				// Outbound connection for contact request; send request message
-				log.Printf("Sending outbound contact request to %v", c)
-				// XXX-protocol ooooohhhhh no you don't. Cannot interact w/ protocol here, because process may
-				// not have started yet. Maybe this one needs to go w/ outbound auth in pre-connection also
-				// honestly, it would not be a bad thing to have outbound unaccepted requests _not_ be
-				// considered active connections, as long as they get handled properly.
-				// c.connection.SendContactRequest(5, c.data.Request.MyNickname, c.data.Request.Message)
-			} else {
-				// Inbound connection implicitly accepts the contact request and can continue as a contact
-				log.Printf("Contact request implicitly accepted by contact %v", c)
-				c.updateContactRequest("Accepted")
-			}
+		if c.data.Request.Pending && c.connection.IsInbound {
+			// Inbound connection implicitly accepts the contact request and can continue as a contact
+			// Outbound request logic is all handled by connectOutbound.
+			log.Printf("Contact request implicitly accepted by contact %v", c)
+			c.updateContactRequest("Accepted")
 		} else {
 			c.status = ricochet.Contact_ONLINE
 		}