diff --git a/lib/session/call-session.js b/lib/session/call-session.js
index e32dd4d0..1c2907ca 100644
--- a/lib/session/call-session.js
+++ b/lib/session/call-session.js
@@ -1744,7 +1744,7 @@ Duration=${duration} `
           res.send(200, {body: this.ep.local.sdp});
         }
         else {
-          if (this.currentTask.name === TaskName.Dial && this.currentTask.isOnHold) {
+          if (this.currentTask.name === TaskName.Dial && this.currentTask.isOnHoldEnabled) {
             this.logger.info('onholdMusic reINVITE after media has been released');
             await this.currentTask.handleReinviteAfterMediaReleased(req, res);
           } else {
diff --git a/lib/tasks/dial.js b/lib/tasks/dial.js
index 96df3a9e..f9975e60 100644
--- a/lib/tasks/dial.js
+++ b/lib/tasks/dial.js
@@ -138,13 +138,14 @@ class TaskDial extends Task {
 
   get name() { return TaskName.Dial; }
 
-  get isOnHold() {
-    return this.isIncomingLegHold || this.isOutgoingLegHold;
+  get isOnHoldEnabled() {
+    return !!this.data.onHoldHook;
   }
 
   get canReleaseMedia() {
     const keepAnchor = this.data.anchorMedia ||
     this.cs.isBackGroundListen ||
+    this.cs.onHoldMusic ||
     ANCHOR_MEDIA_ALWAYS ||
     this.listenTask ||
     this.transcribeTask ||
@@ -570,7 +571,8 @@ class TaskDial extends Task {
           accountInfo: cs.accountInfo,
           rootSpan: cs.rootSpan,
           startSpan: this.startSpan.bind(this),
-          dialTask: this
+          dialTask: this,
+          onHoldMusic: this.cs.onHoldMusic
         });
         this.dials.set(sd.callSid, sd);
 
@@ -679,22 +681,43 @@ class TaskDial extends Task {
   async _onReinvite(req, res) {
     try {
       let isHandled = false;
-      if (this.cs.onHoldMusic) {
-        if (isOnhold(req.body) && !this.epOther && !this.ep) {
-          await this.cs.handleReinviteAfterMediaReleased(req, res);
-          // Onhold but media is already released
-          // reconnect A Leg and Response B leg
-          await this.reAnchorMedia(this.cs, this.sd);
-          this.isOutgoingLegHold = true;
+      if (this.isOnHoldEnabled) {
+        if (isOnhold(req.body)) {
+          this.logger.debug('Dial: _onReinvite receive hold Request');
+          if (!this.epOther && !this.ep) {
+            this.logger.debug(`Dial: _onReinvite receive hold Request,
+ media already released, reconnect media server`);
+            // update caller leg for new SDP from callee.
+            await this.cs.handleReinviteAfterMediaReleased(req, res);
+            // Freeswitch media is released, reconnect
+            await this.reAnchorMedia(this.cs, this.sd);
+            this.isOutgoingLegHold = true;
+          } else {
+            this.logger.debug('Dial: _onReinvite receive hold Request, update SDP');
+            const newSdp = await this.ep.modify(req.body);
+            res.send(200, {body: newSdp});
+          }
           isHandled = true;
-          this._onHoldHook();
-        } else if (!isOnhold(req.body) && this.epOther && this.ep && this.isOutgoingLegHold && this.canReleaseMedia) {
-          // Offhold, time to release media
-          const newSdp = await this.ep.modify(req.body);
-          await res.send(200, {body: newSdp});
-          await this._releaseMedia(this.cs, this.sd);
+          // Media already connected, ask for onHoldHook
+          this._onHoldHook(req);
+        } else if (!isOnhold(req.body)) {
+          this.logger.debug('Dial: _onReinvite receive unhold Request');
+          if (this.epOther && this.ep && this.isOutgoingLegHold && this.canReleaseMedia) {
+            this.logger.debug('Dial: _onReinvite receive unhold Request, release media');
+            // Offhold, time to release media
+            const newSdp = await this.ep.modify(req.body);
+            await res.send(200, {body: newSdp});
+            await this._releaseMedia(this.cs, this.sd);
+            this.isOutgoingLegHold = false;
+          } else {
+            this.logger.debug('Dial: _onReinvite receive unhold Request, update media server');
+            const newSdp = await this.ep.modify(req.body);
+            res.send(200, {body: newSdp});
+          }
+          if (this._onHoldSession) {
+            this._onHoldSession.kill();
+          }
           isHandled = true;
-          this.isOutgoingLegHold = false;
         }
       }
       if (!isHandled) {
@@ -811,23 +834,34 @@ class TaskDial extends Task {
     this.epOther = cs.ep;
   }
 
+  // Handle RE-INVITE hold from caller leg.
   async handleReinviteAfterMediaReleased(req, res) {
     let isHandled = false;
-    if (isOnhold(req.body) && !this.epOther && !this.ep) {
-      const sdp = await this.dlg.modify(req.body);
-      res.send(200, {body: sdp});
-      // Onhold but media is already released
-      await this.reAnchorMedia(this.cs, this.sd);
-      isHandled = true;
-      this.isIncomingLegHold = true;
-      this._onHoldHook();
-    } else if (!isOnhold(req.body) && this.epOther && this.ep && this.isIncomingLegHold && this.canReleaseMedia) {
-      // Offhold, time to release media
-      const newSdp = await this.epOther.modify(req.body);
-      await res.send(200, {body: newSdp});
-      await this._releaseMedia(this.cs, this.sd);
-      isHandled = true;
-      this.isIncomingLegHold = false;
+    if (this.isOnHoldEnabled) {
+      if (isOnhold(req.body)) {
+        if (!this.epOther && !this.ep) {
+          // update callee leg for new SDP from caller.
+          const sdp = await this.dlg.modify(req.body);
+          res.send(200, {body: sdp});
+          // Onhold but media is already released, reconnect
+          await this.reAnchorMedia(this.cs, this.sd);
+          isHandled = true;
+          this.isIncomingLegHold = true;
+        }
+        this._onHoldHook(req);
+      } else if (!isOnhold(req.body)) {
+        if (this.epOther && this.ep && this.isIncomingLegHold && this.canReleaseMedia) {
+          // Offhold, time to release media
+          const newSdp = await this.epOther.modify(req.body);
+          await res.send(200, {body: newSdp});
+          await this._releaseMedia(this.cs, this.sd);
+          isHandled = true;
+        }
+        this.isIncomingLegHold = false;
+        if (this._onHoldSession) {
+          this._onHoldSession.kill();
+        }
+      }
     }
 
     if (!isHandled) {
@@ -846,7 +880,7 @@ class TaskDial extends Task {
       });
   }
 
-  async _onHoldHook(allowed = [TaskName.Play, TaskName.Say, TaskName.Pause]) {
+  async _onHoldHook(req, allowed = [TaskName.Play, TaskName.Say, TaskName.Pause]) {
     if (this.data.onHoldHook) {
       // send silence for keep Voice quality
       await this.epOther.play('silence_stream://500');
@@ -856,7 +890,13 @@ class TaskDial extends Task {
           const b3 = this.getTracingPropagation();
           const httpHeaders = b3 && {b3};
           const json = await this.cs.application.requestor.
-            request('verb:hook', this.data.onHoldHook, this.cs.callInfo.toJSON(), httpHeaders);
+            request('verb:hook', this.data.onHoldHook, {
+              ...this.cs.callInfo.toJSON(),
+              hold_detail: {
+                from: req.get('From'),
+                to: req.get('To')
+              }
+            }, httpHeaders);
           const tasks = normalizeJambones(this.logger, json).map((tdata) => makeTask(this.logger, tdata));
           allowedTasks = tasks.filter((t) => allowed.includes(t.name));
           if (tasks.length !== allowedTasks.length) {
@@ -865,7 +905,7 @@ class TaskDial extends Task {
           }
           this.logger.debug(`DialTask:_onHoldHook: executing ${tasks.length} tasks`);
           if (tasks.length) {
-            this._playSession = new ConfirmCallSession({
+            this._onHoldSession = new ConfirmCallSession({
               logger: this.logger,
               application: this.cs.application,
               dlg: this.isIncomingLegHold ? this.dlg : this.cs.dlg,
@@ -875,12 +915,12 @@ class TaskDial extends Task {
               tasks,
               rootSpan: this.cs.rootSpan
             });
-            await this._playSession.exec();
-            this._playSession = null;
+            await this._onHoldSession.exec();
+            this._onHoldSession = null;
           }
         } catch (error) {
           this.logger.info(error, 'DialTask:_onHoldHook: failed retrieving waitHook');
-          this._playSession = null;
+          this._onHoldSession = null;
           break;
         }
       } while (allowedTasks && allowedTasks.length > 0 && !this.killed && this.isOnHold);
diff --git a/lib/utils/place-outdial.js b/lib/utils/place-outdial.js
index 823704e5..c45e281c 100644
--- a/lib/utils/place-outdial.js
+++ b/lib/utils/place-outdial.js
@@ -18,7 +18,8 @@ const WsRequestor = require('./ws-requestor');
 const {makeOpusFirst} = require('./sdp-utils');
 
 class SingleDialer extends Emitter {
-  constructor({logger, sbcAddress, target, opts, application, callInfo, accountInfo, rootSpan, startSpan, dialTask}) {
+  constructor({logger, sbcAddress, target, opts, application, callInfo, accountInfo, rootSpan, startSpan, dialTask,
+    onHoldMusic}) {
     super();
     assert(target.type);
 
@@ -41,6 +42,7 @@ class SingleDialer extends Emitter {
 
     this.callSid = uuidv4();
     this.dialTask = dialTask;
+    this.onHoldMusic = onHoldMusic;
 
     this.on('callStatusChange', this._notifyCallStatusChange.bind(this));
   }
@@ -131,6 +133,7 @@ class SingleDialer extends Emitter {
       this.serviceUrl = srf.locals.serviceUrl;
 
       this.ep = await ms.createEndpoint();
+      this._configMsEndpoint();
       this.logger.debug(`SingleDialer:exec - created endpoint ${this.ep.uuid}`);
 
       /**
@@ -253,7 +256,7 @@ class SingleDialer extends Emitter {
         .on('modify', async(req, res) => {
           try {
             if (this.ep) {
-              if (this.dialTask && this.dialTask.isOnHold) {
+              if (this.dialTask && this.dialTask.isOnHoldEnabled) {
                 this.logger.info('dial is onhold, emit event');
                 this.emit('reinvite', req, res);
               } else {
@@ -320,6 +323,12 @@ class SingleDialer extends Emitter {
     }
   }
 
+  _configMsEndpoint() {
+    if (this.onHoldMusic) {
+      this.ep.set({hold_music: `shout://${this.onHoldMusic.replace(/^https?:\/\//, '')}`});
+    }
+  }
+
   /**
    * Run an application on the call after answer, e.g. call screening.
    * Once the application completes in some fashion, emit an 'accepted' event
@@ -436,6 +445,7 @@ class SingleDialer extends Emitter {
   async reAnchorMedia() {
     assert(this.dlg && this.dlg.connected && !this.ep);
     this.ep = await this.ms.createEndpoint({remoteSdp: this.dlg.remote.sdp});
+    this._configMsEndpoint();
     await this.dlg.modify(this.ep.local.sdp, {
       headers: {
         'X-Reason': 'anchor-media'
@@ -466,11 +476,12 @@ class SingleDialer extends Emitter {
 }
 
 function placeOutdial({
-  logger, srf, ms, sbcAddress, target, opts, application, callInfo, accountInfo, rootSpan, startSpan, dialTask
+  logger, srf, ms, sbcAddress, target, opts, application, callInfo, accountInfo, rootSpan, startSpan, dialTask,
+  onHoldMusic
 }) {
   const myOpts = deepcopy(opts);
   const sd = new SingleDialer({
-    logger, sbcAddress, target, myOpts, application, callInfo, accountInfo, rootSpan, startSpan, dialTask
+    logger, sbcAddress, target, myOpts, application, callInfo, accountInfo, rootSpan, startSpan, dialTask, onHoldMusic
   });
   sd.exec(srf, ms, myOpts);
   return sd;