diff --git a/apps/web/src/app/billing/organizations/organization-subscription-selfhost.component.html b/apps/web/src/app/billing/organizations/organization-subscription-selfhost.component.html
index 08fb12e76e..03771c5896 100644
--- a/apps/web/src/app/billing/organizations/organization-subscription-selfhost.component.html
+++ b/apps/web/src/app/billing/organizations/organization-subscription-selfhost.component.html
@@ -22,25 +22,45 @@
   [providerName]="userOrg.providerName"
 ></app-org-subscription-hidden>
 
-<ng-container *ngIf="sub && firstLoaded">
+<ng-container *ngIf="subscription && firstLoaded">
   <dl>
     <dt>{{ "billingPlan" | i18n }}</dt>
-    <dd>{{ sub.plan.name }}</dd>
-    <dt>{{ "expiration" | i18n }}</dt>
-    <dd *ngIf="sub.expiration">
-      {{ sub.expiration | date : "mediumDate" }}
-      <span *ngIf="isExpired" class="text-danger ml-2">
-        <i class="bwi bwi-exclamation-triangle" aria-hidden="true"></i>
-        {{ "licenseIsExpired" | i18n }}
-      </span>
-    </dd>
-    <dd *ngIf="!sub.expiration">{{ "neverExpires" | i18n }}</dd>
+    <dd>{{ subscription.planName }}</dd>
     <ng-container *ngIf="billingSyncSetUp">
       <dt>{{ "lastLicenseSync" | i18n }}</dt>
       <dd>
         {{ lastLicenseSync != null ? (lastLicenseSync | date : "medium") : ("never" | i18n) }}
       </dd>
     </ng-container>
+    <dt>
+      <span [ngClass]="{ 'tw-text-danger': showAsExpired }">{{
+        "subscriptionExpiration" | i18n
+      }}</span>
+      <a
+        href="https://bitwarden.com/help/licensing-on-premise/#update-a-renewed-organization-license "
+        target="_blank"
+        [appA11yTitle]="'licensePaidFeaturesHelp' | i18n"
+        rel="noopener"
+      >
+        <i class="bwi bwi-question-circle" aria-hidden="true"></i>
+        <span class="sr-only">{{ "licensePaidFeaturesHelp" | i18n }}</span>
+      </a>
+    </dt>
+    <dd *ngIf="subscription.hasExpiration" [ngClass]="{ 'tw-text-danger': showAsExpired }">
+      {{
+        (subscription.hasSeparateGracePeriod
+          ? subscription.expirationWithoutGracePeriod
+          : subscription.expirationWithGracePeriod
+        ) | date : "mediumDate"
+      }}
+      <div *ngIf="subscription.hasSeparateGracePeriod" class="tw-text-muted">
+        {{
+          "selfHostGracePeriodHelp"
+            | i18n : (subscription.expirationWithGracePeriod | date : "mediumDate")
+        }}
+      </div>
+    </dd>
+    <dd *ngIf="!subscription.hasExpiration">{{ "neverExpires" | i18n }}</dd>
   </dl>
 
   <a
diff --git a/apps/web/src/app/billing/organizations/organization-subscription-selfhost.component.ts b/apps/web/src/app/billing/organizations/organization-subscription-selfhost.component.ts
index a6afb20aad..fb01d07c59 100644
--- a/apps/web/src/app/billing/organizations/organization-subscription-selfhost.component.ts
+++ b/apps/web/src/app/billing/organizations/organization-subscription-selfhost.component.ts
@@ -1,7 +1,7 @@
 import { Component, OnDestroy, OnInit } from "@angular/core";
 import { FormControl, FormGroup } from "@angular/forms";
 import { ActivatedRoute } from "@angular/router";
-import { concatMap, takeUntil, Subject } from "rxjs";
+import { concatMap, Subject, takeUntil } from "rxjs";
 
 import { ModalConfig, ModalService } from "@bitwarden/angular/services/modal.service";
 import { ApiService } from "@bitwarden/common/abstractions/api.service";
@@ -14,7 +14,7 @@ import { OrganizationConnectionType } from "@bitwarden/common/admin-console/enum
 import { Organization } from "@bitwarden/common/admin-console/models/domain/organization";
 import { OrganizationConnectionResponse } from "@bitwarden/common/admin-console/models/response/organization-connection.response";
 import { BillingSyncConfigApi } from "@bitwarden/common/billing/models/api/billing-sync-config.api";
-import { OrganizationSubscriptionResponse } from "@bitwarden/common/billing/models/response/organization-subscription.response";
+import { SelfHostedOrganizationSubscriptionView } from "@bitwarden/common/billing/models/view/self-hosted-organization-subscription.view";
 
 import {
   BillingSyncKeyComponent,
@@ -31,7 +31,7 @@ enum LicenseOptions {
   templateUrl: "organization-subscription-selfhost.component.html",
 })
 export class OrganizationSubscriptionSelfhostComponent implements OnInit, OnDestroy {
-  sub: OrganizationSubscriptionResponse;
+  subscription: SelfHostedOrganizationSubscriptionView;
   organizationId: string;
   userOrg: Organization;
 
@@ -65,6 +65,15 @@ export class OrganizationSubscriptionSelfhostComponent implements OnInit, OnDest
     return this.existingBillingSyncConnection?.enabled;
   }
 
+  /**
+   * Render the subscription as expired.
+   */
+  get showAsExpired() {
+    return this.subscription.hasSeparateGracePeriod
+      ? this.subscription.isExpiredWithoutGracePeriod
+      : this.subscription.isExpiredAndOutsideGracePeriod;
+  }
+
   constructor(
     private modalService: ModalService,
     private messagingService: MessagingService,
@@ -102,7 +111,10 @@ export class OrganizationSubscriptionSelfhostComponent implements OnInit, OnDest
     this.loading = true;
     this.userOrg = this.organizationService.get(this.organizationId);
     if (this.userOrg.canViewSubscription) {
-      this.sub = await this.organizationApiService.getSubscription(this.organizationId);
+      const subscriptionResponse = await this.organizationApiService.getSubscription(
+        this.organizationId
+      );
+      this.subscription = new SelfHostedOrganizationSubscriptionView(subscriptionResponse);
     }
 
     this.loading = false;
@@ -159,10 +171,6 @@ export class OrganizationSubscriptionSelfhostComponent implements OnInit, OnDest
     return this.existingBillingSyncConnection?.id != null;
   }
 
-  get isExpired() {
-    return this.sub?.expiration != null && new Date(this.sub.expiration) < new Date();
-  }
-
   get updateMethod() {
     return this.form.get("updateMethod").value;
   }
diff --git a/apps/web/src/locales/en/messages.json b/apps/web/src/locales/en/messages.json
index fdb28832fd..1f0f366fbf 100644
--- a/apps/web/src/locales/en/messages.json
+++ b/apps/web/src/locales/en/messages.json
@@ -6553,6 +6553,18 @@
   "billingSyncHelp": {
     "message": "Billing Sync help"
   },
+  "licensePaidFeaturesHelp": {
+    "message": "License paid features help"
+  },
+  "selfHostGracePeriodHelp": {
+    "message": "After your subscription expires, you have 60 days to apply an updated license file to your organization. Grace period ends $GRACE_PERIOD_END_DATE$.",
+    "placeholders": {
+      "GRACE_PERIOD_END_DATE": {
+        "content": "$1",
+        "example": "May 12, 2024"
+      }
+    }
+  },
   "uploadLicense": {
     "message": "Upload license"
   },
diff --git a/libs/common/src/billing/models/response/organization-subscription.response.ts b/libs/common/src/billing/models/response/organization-subscription.response.ts
index 09c9f3a758..35d66bba04 100644
--- a/libs/common/src/billing/models/response/organization-subscription.response.ts
+++ b/libs/common/src/billing/models/response/organization-subscription.response.ts
@@ -11,6 +11,7 @@ export class OrganizationSubscriptionResponse extends OrganizationResponse {
   subscription: BillingSubscriptionResponse;
   upcomingInvoice: BillingSubscriptionUpcomingInvoiceResponse;
   expiration: string;
+  expirationWithoutGracePeriod: string;
 
   constructor(response: any) {
     super(response);
@@ -24,5 +25,6 @@ export class OrganizationSubscriptionResponse extends OrganizationResponse {
         ? null
         : new BillingSubscriptionUpcomingInvoiceResponse(upcomingInvoice);
     this.expiration = this.getResponseProperty("Expiration");
+    this.expirationWithoutGracePeriod = this.getResponseProperty("ExpirationWithoutGracePeriod");
   }
 }
diff --git a/libs/common/src/billing/models/view/self-hosted-organization-subscription.view.ts b/libs/common/src/billing/models/view/self-hosted-organization-subscription.view.ts
new file mode 100644
index 0000000000..c1f5640207
--- /dev/null
+++ b/libs/common/src/billing/models/view/self-hosted-organization-subscription.view.ts
@@ -0,0 +1,61 @@
+import { View } from "../../../models/view/view";
+import { OrganizationSubscriptionResponse } from "../response/organization-subscription.response";
+
+export class SelfHostedOrganizationSubscriptionView implements View {
+  planName: string;
+
+  /**
+   * Date the subscription expires, including the grace period.
+   */
+  expirationWithGracePeriod?: Date;
+
+  /**
+   * Date the subscription expires, excluding the grace period.
+   * This will be `null` for older (< v12) license files because they do not include this date.
+   * In this case, you have to rely on the `expirationWithGracePeriod` instead.
+   */
+  expirationWithoutGracePeriod?: Date;
+
+  constructor(response: OrganizationSubscriptionResponse) {
+    if (response == null) {
+      return;
+    }
+
+    this.planName = response.plan.name;
+    this.expirationWithGracePeriod =
+      response.expiration != null ? new Date(response.expiration) : null;
+    this.expirationWithoutGracePeriod =
+      response.expirationWithoutGracePeriod != null
+        ? new Date(response.expirationWithoutGracePeriod)
+        : null;
+  }
+
+  /**
+   * The subscription has separate expiration dates for the subscription and the end of grace period.
+   */
+  get hasSeparateGracePeriod() {
+    return this.expirationWithGracePeriod != null && this.expirationWithoutGracePeriod != null;
+  }
+
+  /**
+   * True if the subscription has an expiration date.
+   */
+  get hasExpiration() {
+    return this.expirationWithGracePeriod != null;
+  }
+
+  /**
+   * True if the subscription has an expiration date that has past, but may still be within the grace period.
+   * For older licenses (< v12), this will always be false because they do not include the `expirationWithoutGracePeriod`.
+   */
+  get isExpiredWithoutGracePeriod() {
+    return this.hasSeparateGracePeriod && this.expirationWithoutGracePeriod < new Date();
+  }
+
+  /**
+   * True if the subscription has an expiration date that has past, including the grace period.
+   */
+  get isExpiredAndOutsideGracePeriod() {
+    return this.hasExpiration && this.expirationWithGracePeriod < new Date();
+  }
+}