diff --git a/lib/session/call-session.js b/lib/session/call-session.js
index a1a2aaee..f9639739 100644
--- a/lib/session/call-session.js
+++ b/lib/session/call-session.js
@@ -115,6 +115,7 @@ class CallSession extends Emitter {
       this.logger.debug(`CallSession: ${this.callSid} listener count ${this.requestor.listenerCount('command')}`);
       this.requestor.on('connection-dropped', this._onWsConnectionDropped.bind(this));
       this.requestor.on('handover', handover.bind(this));
+      this.requestor.on('reconnect-error', this._onSessionReconnectError.bind(this));
     };
 
     if (!this.isConfirmCallSession) {
@@ -122,6 +123,7 @@ class CallSession extends Emitter {
       this.logger.debug(`CallSession: ${this.callSid} listener count ${this.requestor.listenerCount('command')}`);
       this.requestor.on('connection-dropped', this._onWsConnectionDropped.bind(this));
       this.requestor.on('handover', handover.bind(this));
+      this.requestor.on('reconnect-error', this._onSessionReconnectError.bind(this));
     }
   }
 
@@ -1704,6 +1706,22 @@ Duration=${duration} `
     }, 'CallSession:_injectTasks - completed');
   }
 
+  async _onSessionReconnectError(err) {
+    const {writeAlerts, AlertType} = this.srf.locals;
+    const sid = this.accountInfo.account.account_sid;
+    this.logger.info({err}, `_onSessionReconnectError for account ${sid}`);
+    try {
+      await writeAlerts({
+        alert_type: AlertType.WEBHOOK_CONNECTION_FAILURE,
+        account_sid: this.accountSid,
+        detail: `Session:reconnect error ${err}`
+      });
+    } catch (error) {
+      this.logger.error({error}, 'Error writing WEBHOOK_CONNECTION_FAILURE alert');
+    }
+    this._jambonzHangup();
+  }
+
   _onCommand({msgid, command, call_sid, queueCommand, data}) {
     this.logger.info({msgid, command, queueCommand, data}, 'CallSession:_onCommand - received command');
     let resolution;
diff --git a/lib/utils/ws-requestor.js b/lib/utils/ws-requestor.js
index 3d7e3b69..d5c8645f 100644
--- a/lib/utils/ws-requestor.js
+++ b/lib/utils/ws-requestor.js
@@ -56,6 +56,12 @@ class WsRequestor extends BaseRequestor {
     }
 
     if (type === 'session:new') this.call_sid = params.callSid;
+    if (type === 'session:reconnect') {
+      this._reconnectPromise = new Promise((resolve, reject) => {
+        this._reconnectResolve = resolve;
+        this._reconnectReject = reject;
+      });
+    }
 
     /* if we have an absolute url, and it is http then do a standard webhook */
     if (this._isAbsoluteUrl(url) && url.startsWith('http')) {
@@ -71,20 +77,23 @@ class WsRequestor extends BaseRequestor {
     }
 
     /* connect if necessary */
+    const queueMsg = () => {
+      this.logger.debug(
+        `WsRequestor:request(${this.id}) - queueing ${type} message since we are connecting`);
+      if (wantsAck) {
+        const p = new Promise((resolve, reject) => {
+          this.queuedMsg.push({type, hook, params, httpHeaders, promise: {resolve, reject}});
+        });
+        return p;
+      }
+      else {
+        this.queuedMsg.push({type, hook, params, httpHeaders});
+      }
+      return;
+    };
     if (!this.ws) {
       if (this.connectInProgress) {
-        this.logger.debug(
-          `WsRequestor:request(${this.id}) - queueing ${type} message since we are connecting`);
-        if (wantsAck) {
-          const p = new Promise((resolve, reject) => {
-            this.queuedMsg.push({type, hook, params, httpHeaders, promise: {resolve, reject}});
-          });
-          return p;
-        }
-        else {
-          this.queuedMsg.push({type, hook, params, httpHeaders});
-        }
-        return;
+        return queueMsg();
       }
       this.connectInProgress = true;
       this.logger.debug(`WsRequestor:request(${this.id}) - connecting since we do not have a connection for ${type}`);
@@ -102,6 +111,10 @@ class WsRequestor extends BaseRequestor {
         return Promise.reject(err);
       }
     }
+    // If jambonz wait for ack from reconnect, queue the msg until reconnect is acked
+    if (type !== 'session:reconnect' && this._reconnectPromise) {
+      return queueMsg();
+    }
     assert(this.ws);
 
     /* prepare and send message */
@@ -139,6 +152,18 @@ class WsRequestor extends BaseRequestor {
       }
     };
 
+    const rejectQueuedMsgs = (err) => {
+      if (this.queuedMsg.length > 0) {
+        for (const {promise} of this.queuedMsg) {
+          this.logger.debug(`WsRequestor:request - preparing queued ${type} for rejectQueuedMsgs`);
+          if (promise) {
+            promise.reject(err);
+          }
+        }
+        this.queuedMsg.length = 0;
+      }
+    };
+
     //this.logger.debug({obj}, `websocket: sending (${url})`);
 
     /* special case: reconnecting before we received ack to session:new */
@@ -179,16 +204,37 @@ class WsRequestor extends BaseRequestor {
           this.logger.debug({response}, `WsRequestor:request ${url} succeeded in ${rtt}ms`);
           this.stats.histogram('app.hook.ws_response_time', rtt, ['hook_type:app']);
           resolve(response);
+          if (this._reconnectResolve) {
+            this._reconnectResolve();
+          }
         },
         failure: (err) => {
+          if (this._reconnectReject) {
+            this._reconnectReject(err);
+          }
           clearTimeout(timer);
           reject(err);
         }
       });
 
       /* send the message */
-      this.ws.send(JSON.stringify(obj), () => {
+      this.ws.send(JSON.stringify(obj), async() => {
         this.logger.debug({obj}, `WsRequestor:request websocket: sent (${url})`);
+        // If session:reconnect is waiting for ack, hold here until ack to send queuedMsgs
+        if (this._reconnectPromise) {
+          try {
+            await this._reconnectPromise;
+          } catch (err) {
+            // bad thing happened to session:recconnect
+            rejectQueuedMsgs(err);
+            this.emit('reconnect-error');
+            return;
+          } finally {
+            this._reconnectPromise = null;
+            this._reconnectResolve = null;
+            this._reconnectReject = null;
+          }
+        }
         sendQueuedMsgs();
       });
     });