diff --git a/src/libs/ReportUtils.js b/src/libs/ReportUtils.js
index 764699947a97..a384d5e54b9f 100644
--- a/src/libs/ReportUtils.js
+++ b/src/libs/ReportUtils.js
@@ -577,6 +577,16 @@ function isDM(report) {
     return !getChatType(report);
 }
 
+/**
+ * Returns true if report has a single participant.
+ *
+ * @param {Object} report
+ * @returns {Boolean}
+ */
+function hasSingleParticipant(report) {
+    return report.participants && report.participants.length === 1;
+}
+
 /**
  * If the report is a thread and has a chat type set, it is a workspace chat.
  *
@@ -2398,6 +2408,7 @@ function getMoneyRequestOptions(report, reportParticipants, betas) {
     const participants = _.filter(reportParticipants, (accountID) => currentUserPersonalDetails.accountID !== accountID);
 
     const hasExcludedIOUAccountIDs = lodashIntersection(reportParticipants, CONST.EXPENSIFY_ACCOUNT_IDS).length > 0;
+    const hasSingleParticipantInReport = participants.length === 1;
     const hasMultipleParticipants = participants.length > 1;
 
     if (hasExcludedIOUAccountIDs || (participants.length === 0 && !report.isOwnPolicyExpenseChat)) {
@@ -2423,7 +2434,7 @@ function getMoneyRequestOptions(report, reportParticipants, betas) {
         ...(canRequestMoney(report) ? [CONST.IOU.MONEY_REQUEST_TYPE.REQUEST] : []),
 
         // Send money option should be visible only in DMs
-        ...(Permissions.canUseIOUSend(betas) && isChatReport(report) && !isPolicyExpenseChat(report) && participants.length === 1 ? [CONST.IOU.MONEY_REQUEST_TYPE.SEND] : []),
+        ...(Permissions.canUseIOUSend(betas) && isChatReport(report) && !isPolicyExpenseChat(report) && hasSingleParticipantInReport ? [CONST.IOU.MONEY_REQUEST_TYPE.SEND] : []),
     ];
 }
 
@@ -2711,6 +2722,8 @@ export {
     getOriginalReportID,
     canAccessReport,
     getReportOfflinePendingActionAndErrors,
+    isDM,
     getPolicy,
     shouldDisableRename,
+    hasSingleParticipant,
 };
diff --git a/src/libs/actions/Task.js b/src/libs/actions/Task.js
index b3dd76a38d78..32ffa759fa16 100644
--- a/src/libs/actions/Task.js
+++ b/src/libs/actions/Task.js
@@ -13,6 +13,7 @@ import * as UserUtils from '../UserUtils';
 import * as ErrorUtils from '../ErrorUtils';
 import * as ReportActionsUtils from '../ReportActionsUtils';
 import * as Expensicons from '../../components/Icon/Expensicons';
+import * as LocalePhoneNumber from '../LocalePhoneNumber';
 
 let currentUserEmail;
 let currentUserAccountID;
@@ -597,10 +598,16 @@ function getAssignee(details) {
  * */
 function getShareDestination(reportID, reports, personalDetails) {
     const report = lodashGet(reports, `report_${reportID}`, {});
+    let subtitle = '';
+    if (ReportUtils.isChatReport(report) && ReportUtils.isDM(report) && ReportUtils.hasSingleParticipant(report)) {
+        subtitle = LocalePhoneNumber.formatPhoneNumber(report.participants[0]);
+    } else {
+        subtitle = ReportUtils.getChatRoomSubtitle(report);
+    }
     return {
         icons: ReportUtils.getIcons(report, personalDetails, Expensicons.FallbackAvatar, ReportUtils.isIOUReport(report)),
         displayName: ReportUtils.getReportName(report),
-        subtitle: ReportUtils.getChatRoomSubtitle(report),
+        subtitle,
     };
 }
 
diff --git a/src/pages/home/HeaderView.js b/src/pages/home/HeaderView.js
index bc8cf0fed584..7622a0e73f18 100644
--- a/src/pages/home/HeaderView.js
+++ b/src/pages/home/HeaderView.js
@@ -91,8 +91,8 @@ function HeaderView(props) {
     const title = ReportUtils.getReportName(reportHeaderData);
     const subtitle = ReportUtils.getChatRoomSubtitle(reportHeaderData);
     const parentNavigationSubtitle = ReportUtils.getParentNavigationSubtitle(reportHeaderData);
-    const isConcierge = participants.length === 1 && _.contains(participants, CONST.ACCOUNT_ID.CONCIERGE);
-    const isAutomatedExpensifyAccount = participants.length === 1 && ReportUtils.hasAutomatedExpensifyAccountIDs(participants);
+    const isConcierge = ReportUtils.hasSingleParticipant(props.report) && _.contains(participants, CONST.ACCOUNT_ID.CONCIERGE);
+    const isAutomatedExpensifyAccount = ReportUtils.hasSingleParticipant(props.report) && ReportUtils.hasAutomatedExpensifyAccountIDs(participants);
     const guideCalendarLink = lodashGet(props.account, 'guideCalendarLink');
 
     // We hide the button when we are chatting with an automated Expensify account since it's not possible to contact