Index: channels/chan_sip.c
===================================================================
--- channels/chan_sip.c	(revision 233049)
+++ channels/chan_sip.c	(working copy)
@@ -3116,6 +3116,9 @@
 			ast_queue_control(p->owner, AST_CONTROL_CONGESTION);
 			ast_channel_unlock(p->owner);
 		}
+
+		/* Give the channel a chance to act before we proceed with destruction */
+		sip_scheddestroy(p, DEFAULT_TRANS_TIMEOUT);
 	}
 	ast_mutex_unlock(&p->lock);
 	return 0;
@@ -3759,18 +3762,19 @@
 			if (ast_test_flag(&p->flags[0], SIP_OUTGOING)) {
 				/* stop retransmitting an INVITE that has not received a response */
 				struct sip_pkt *cur;
-				for (cur = p->packets; cur; cur = cur->next) {
-					__sip_semi_ack(p, cur->seqno, ast_test_flag(cur, FLAG_RESPONSE), cur->method ? cur->method : find_sip_method(cur->data));
-				}
 
 				/* if we can't send right now, mark it pending */
 				if (p->invitestate == INV_CALLING) {
 					/* We can't send anything in CALLING state */
 					ast_set_flag(&p->flags[0], SIP_PENDINGBYE);
+					__sip_pretend_ack(p);
 					/* Do we need a timer here if we don't hear from them at all? Yes we do or else we will get hung dialogs and those are no fun. */
 					sip_scheddestroy(p, DEFAULT_TRANS_TIMEOUT);
 					append_history(p, "DELAY", "Not sending cancel, waiting for timeout");
 				} else {
+					for (cur = p->packets; cur; cur = cur->next) {
+						__sip_semi_ack(p, cur->seqno, ast_test_flag(cur, FLAG_RESPONSE), cur->method ? cur->method : find_sip_method(cur->data));
+					}
 					p->invitestate = INV_CANCELLED;
 					/* Send a new request: CANCEL */
 					transmit_request(p, SIP_CANCEL, p->lastinvite, XMIT_RELIABLE, FALSE);