[PM-7004] Org Admin Initiate Delete (#3905)

* org delete

* move org id to URL path

* tweaks

* lint fixes

* Update src/Core/Services/Implementations/HandlebarsMailService.cs

Co-authored-by: Rui Tomé <108268980+r-tome@users.noreply.github.com>

* Update src/Core/Services/Implementations/HandlebarsMailService.cs

Co-authored-by: Rui Tomé <108268980+r-tome@users.noreply.github.com>

* Apply suggestions from code review

Co-authored-by: Rui Tomé <108268980+r-tome@users.noreply.github.com>

* Apply suggestions from code review

Co-authored-by: Rui Tomé <108268980+r-tome@users.noreply.github.com>

* PR feedback

* fix id

* [PM-7004] Move OrgDeleteTokenable to AdminConsole ownership

* [PM-7004] Add consolidated billing logic into organization delete request acceptance endpoint

* [PM-7004] Delete unused IOrganizationService.DeleteAsync(Organization organization, string token) method

* [PM-7004] Fix unit tests

* [PM-7004] Update delete organization request email templates

* Add success message when initiating organization deletion

* Refactor OrganizationsController request delete initiation action to handle exceptions

---------

Co-authored-by: Rui Tomé <108268980+r-tome@users.noreply.github.com>
Co-authored-by: Rui Tome <rtome@bitwarden.com>

src/Admin/AdminConsole/Controllers/OrganizationsController.cs

@@ -269,6 +269,35 @@ public class OrganizationsController : Controller
         return RedirectToAction("Index");
     }
 
+    [HttpPost]
+    [ValidateAntiForgeryToken]
+    [RequirePermission(Permission.Org_Delete)]
+    public async Task<IActionResult> DeleteInitiation(Guid id, OrganizationInitiateDeleteModel model)
+    {
+        if (!ModelState.IsValid)
+        {
+            TempData["Error"] = ModelState.GetErrorMessage();
+        }
+        else
+        {
+            try
+            {
+                var organization = await _organizationRepository.GetByIdAsync(id);
+                if (organization != null)
+                {
+                    await _organizationService.InitiateDeleteAsync(organization, model.AdminEmail);
+                    TempData["Success"] = "The request to initiate deletion of the organization has been sent.";
+                }
+            }
+            catch (Exception ex)
+            {
+                TempData["Error"] = ex.Message;
+            }
+        }
+
+        return RedirectToAction("Edit", new { id });
+    }
+
     public async Task<IActionResult> TriggerBillingSync(Guid id)
     {
         var organization = await _organizationRepository.GetByIdAsync(id);

src/Admin/AdminConsole/Models/OrganizationInitiateDeleteModel.cs

@@ -0,0 +1,12 @@
+using System.ComponentModel.DataAnnotations;
+
+namespace Bit.Admin.AdminConsole.Models;
+
+public class OrganizationInitiateDeleteModel
+{
+    [Required]
+    [EmailAddress]
+    [StringLength(256)]
+    [Display(Name = "Admin Email")]
+    public string AdminEmail { get; set; }
+}

src/Admin/AdminConsole/Views/Organizations/Edit.cshtml

@@ -1,4 +1,4 @@
-@using Bit.Admin.Enums;
+@using Bit.Admin.Enums;
 @using Bit.Admin.Models
 @using Bit.Core.Enums
 @inject Bit.Admin.Services.IAccessControlService AccessControlService
@@ -18,24 +18,43 @@
 
     <script>
         (() => {
-            document.getElementById('teams-trial').addEventListener('click', () => {
-                if (document.getElementById('@(nameof(Model.PlanType))').value !== '@((byte)PlanType.Free)') {
-                    alert('Organization is not on a free plan.');
-                    return;
-                }
-                setTrialDefaults('@((byte)PlanType.TeamsAnnually)');
-                togglePlanFeatures('@((byte)PlanType.TeamsAnnually)');
-                document.getElementById('@(nameof(Model.Plan))').value = 'Teams (Trial)';
-            });
-            document.getElementById('enterprise-trial').addEventListener('click', () => {
-                if (document.getElementById('@(nameof(Model.PlanType))').value !== '@((byte)PlanType.Free)') {
-                    alert('Organization is not on a free plan.');
-                    return;
-                }
-                setTrialDefaults('@((byte)PlanType.EnterpriseAnnually)');
-                togglePlanFeatures('@((byte)PlanType.EnterpriseAnnually)');
-                document.getElementById('@(nameof(Model.Plan))').value = 'Enterprise (Trial)';
-            });
+            const treamsTrialButton = document.getElementById('teams-trial');
+            if (treamsTrialButton != null) {
+                treamsTrialButton.addEventListener('click', () => {
+                    if (document.getElementById('@(nameof(Model.PlanType))').value !== '@((byte)PlanType.Free)') {
+                        alert('Organization is not on a free plan.');
+                        return;
+                    }
+                    setTrialDefaults('@((byte)PlanType.TeamsAnnually)');
+                    togglePlanFeatures('@((byte)PlanType.TeamsAnnually)');
+                    document.getElementById('@(nameof(Model.Plan))').value = 'Teams (Trial)';
+                });
+            }
+
+            const entTrialButton = document.getElementById('enterprise-trial');
+            if (entTrialButton != null) {
+                entTrialButton.addEventListener('click', () => {
+                    if (document.getElementById('@(nameof(Model.PlanType))').value !== '@((byte)PlanType.Free)') {
+                        alert('Organization is not on a free plan.');
+                        return;
+                    }
+                    setTrialDefaults('@((byte)PlanType.EnterpriseAnnually)');
+                    togglePlanFeatures('@((byte)PlanType.EnterpriseAnnually)');
+                    document.getElementById('@(nameof(Model.Plan))').value = 'Enterprise (Trial)';
+                });
+            }
+
+            const initDeleteButton = document.getElementById('initiate-delete-form');
+            if (initDeleteButton != null) {
+                initDeleteButton.addEventListener('submit', (e) => {
+                    const email = prompt('Enter the email address of the owner/admin that your want to ' +
+                        'request the organization delete verification process with.');
+                    document.getElementById('AdminEmail').value = email;
+                    if (email == null || email === '') {
+                        e.preventDefault();
+                    }
+                });
+            }
 
             function setTrialDefaults(planType) {
                 // Plan
@@ -76,7 +95,7 @@
 {
     <h2>Billing Information</h2>
     @await Html.PartialAsync("_BillingInformation",
-        new BillingInformationModel { BillingInfo = Model.BillingInfo, OrganizationId = Model.Organization.Id, Entity = "Organization" })
+                new BillingInformationModel { BillingInfo = Model.BillingInfo, OrganizationId = Model.Organization.Id, Entity = "Organization" })
 }
 
 @await Html.PartialAsync("~/AdminConsole/Views/Shared/_OrganizationForm.cshtml", Model)
@@ -95,18 +114,20 @@
         }
         @if (canUnlinkFromProvider && Model.Provider is not null)
         {
-            <button
-                class="btn btn-outline-danger mr-2"
-                onclick="return unlinkProvider('@Model.Organization.Id');"
-            >
+            <button class="btn btn-outline-danger mr-2"
+                    onclick="return unlinkProvider('@Model.Organization.Id');">
                 Unlink provider
             </button>
         }
         @if (canDelete)
         {
+            <form asp-action="DeleteInitiation" asp-route-id="@Model.Organization.Id" id="initiate-delete-form">
+                <input type="hidden" name="AdminEmail" id="AdminEmail" />
+                <button class="btn btn-danger mr-2" type="submit">Request Delete</button>
+            </form>
             <form asp-action="Delete" asp-route-id="@Model.Organization.Id"
-                onsubmit="return confirm('Are you sure you want to delete this organization?')">
-                <button class="btn btn-danger" type="submit">Delete</button>
+                  onsubmit="return confirm('Are you sure you want to hard delete this organization?')">
+                <button class="btn btn-outline-danger" type="submit">Delete</button>
             </form>
         }
     </div>

src/Admin/Views/Shared/_Layout.cshtml

@@ -174,6 +174,14 @@
             });
         </script>
     }
+    @if (TempData["Success"] != null)
+    {
+        <script>
+            $(document).ready(function () {
+                toastr.success("@TempData["Success"]")
+            });
+        </script>
+    }
 
     @RenderSection("Scripts", required: false)
 </body>

src/Api/AdminConsole/Controllers/OrganizationsController.cs

@@ -11,6 +11,7 @@ using Bit.Api.Models.Request.Organizations;
 using Bit.Api.Models.Response;
 using Bit.Core;
 using Bit.Core.AdminConsole.Enums;
+using Bit.Core.AdminConsole.Models.Business.Tokenables;
 using Bit.Core.AdminConsole.Models.Data.Organizations.Policies;
 using Bit.Core.AdminConsole.OrganizationFeatures.OrganizationApiKeys.Interfaces;
 using Bit.Core.AdminConsole.OrganizationFeatures.OrganizationCollectionEnhancements.Interfaces;
@@ -26,6 +27,7 @@ using Bit.Core.Exceptions;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
 using Bit.Core.Settings;
+using Bit.Core.Tokens;
 using Bit.Core.Utilities;
 using Microsoft.AspNetCore.Authorization;
 using Microsoft.AspNetCore.Mvc;
@@ -54,6 +56,7 @@ public class OrganizationsController : Controller
     private readonly IOrganizationEnableCollectionEnhancementsCommand _organizationEnableCollectionEnhancementsCommand;
     private readonly IProviderRepository _providerRepository;
     private readonly IScaleSeatsCommand _scaleSeatsCommand;
+    private readonly IDataProtectorTokenFactory<OrgDeleteTokenable> _orgDeleteTokenDataFactory;
 
     public OrganizationsController(
         IOrganizationRepository organizationRepository,
@@ -73,7 +76,8 @@ public class OrganizationsController : Controller
         IPushNotificationService pushNotificationService,
         IOrganizationEnableCollectionEnhancementsCommand organizationEnableCollectionEnhancementsCommand,
         IProviderRepository providerRepository,
-        IScaleSeatsCommand scaleSeatsCommand)
+        IScaleSeatsCommand scaleSeatsCommand,
+        IDataProtectorTokenFactory<OrgDeleteTokenable> orgDeleteTokenDataFactory)
     {
         _organizationRepository = organizationRepository;
         _organizationUserRepository = organizationUserRepository;
@@ -93,6 +97,7 @@ public class OrganizationsController : Controller
         _organizationEnableCollectionEnhancementsCommand = organizationEnableCollectionEnhancementsCommand;
         _providerRepository = providerRepository;
         _scaleSeatsCommand = scaleSeatsCommand;
+        _orgDeleteTokenDataFactory = orgDeleteTokenDataFactory;
     }
 
     [HttpGet("{id}")]
@@ -279,6 +284,37 @@ public class OrganizationsController : Controller
         await _organizationService.DeleteAsync(organization);
     }
 
+    [HttpPost("{id}/delete-recover-token")]
+    [AllowAnonymous]
+    public async Task PostDeleteRecoverToken(Guid id, [FromBody] OrganizationVerifyDeleteRecoverRequestModel model)
+    {
+        var organization = await _organizationRepository.GetByIdAsync(id);
+        if (organization == null)
+        {
+            throw new NotFoundException();
+        }
+
+        if (!_orgDeleteTokenDataFactory.TryUnprotect(model.Token, out var data) || !data.IsValid(organization))
+        {
+            throw new BadRequestException("Invalid token.");
+        }
+
+        var consolidatedBillingEnabled = _featureService.IsEnabled(FeatureFlagKeys.EnableConsolidatedBilling);
+        if (consolidatedBillingEnabled && organization.IsValidClient())
+        {
+            var provider = await _providerRepository.GetByOrganizationIdAsync(organization.Id);
+            if (provider.IsBillable())
+            {
+                await _scaleSeatsCommand.ScalePasswordManagerSeats(
+                    provider,
+                    organization.PlanType,
+                    -organization.Seats ?? 0);
+            }
+        }
+
+        await _organizationService.DeleteAsync(organization);
+    }
+
     [HttpPost("{id}/import")]
     public async Task Import(string id, [FromBody] ImportOrganizationUsersRequestModel model)
     {

src/Api/AdminConsole/Models/Request/Organizations/OrganizationVerifyDeleteRecoverRequestModel.cs

@@ -0,0 +1,9 @@
+using System.ComponentModel.DataAnnotations;
+
+namespace Bit.Api.AdminConsole.Models.Request.Organizations;
+
+public class OrganizationVerifyDeleteRecoverRequestModel
+{
+    [Required]
+    public string Token { get; set; }
+}

src/Core/AdminConsole/Models/Business/Tokenables/OrgDeleteTokenable.cs

@@ -0,0 +1,32 @@
+using System.Text.Json.Serialization;
+using Bit.Core.AdminConsole.Entities;
+
+namespace Bit.Core.AdminConsole.Models.Business.Tokenables;
+
+public class OrgDeleteTokenable : Tokens.ExpiringTokenable
+{
+    public const string ClearTextPrefix = "";
+    public const string DataProtectorPurpose = "OrgDeleteDataProtector";
+    public const string TokenIdentifier = "OrgDelete";
+    public string Identifier { get; set; } = TokenIdentifier;
+    public Guid Id { get; set; }
+
+    [JsonConstructor]
+    public OrgDeleteTokenable(DateTime expirationDate)
+    {
+        ExpirationDate = expirationDate;
+    }
+
+    public OrgDeleteTokenable(Organization organization, int hoursTillExpiration)
+    {
+        Id = organization.Id;
+        ExpirationDate = DateTime.UtcNow.AddHours(hoursTillExpiration);
+    }
+
+    public bool IsValid(Organization organization)
+    {
+        return Id == organization.Id;
+    }
+
+    protected override bool TokenIsValid() => Identifier == TokenIdentifier && Id != default;
+}

src/Core/AdminConsole/Services/IOrganizationService.cs

@@ -34,6 +34,7 @@ public interface IOrganizationService
     /// </summary>
     Task<(Organization organization, OrganizationUser organizationUser)> SignUpAsync(OrganizationLicense license, User owner,
         string ownerKey, string collectionName, string publicKey, string privateKey);
+    Task InitiateDeleteAsync(Organization organization, string orgAdminEmail);
     Task DeleteAsync(Organization organization);
     Task EnableAsync(Guid organizationId, DateTime? expirationDate);
     Task DisableAsync(Guid organizationId, DateTime? expirationDate);

src/Core/AdminConsole/Services/Implementations/OrganizationService.cs

@@ -4,6 +4,7 @@ using Bit.Core.AdminConsole.Entities;
 using Bit.Core.AdminConsole.Enums;
 using Bit.Core.AdminConsole.Enums.Provider;
 using Bit.Core.AdminConsole.Models.Business;
+using Bit.Core.AdminConsole.Models.Business.Tokenables;
 using Bit.Core.AdminConsole.Models.Data.Organizations.Policies;
 using Bit.Core.AdminConsole.OrganizationFeatures.OrganizationUsers.Interfaces;
 using Bit.Core.AdminConsole.Repositories;
@@ -60,6 +61,7 @@ public class OrganizationService : IOrganizationService
     private readonly IProviderUserRepository _providerUserRepository;
     private readonly ICountNewSmSeatsRequiredQuery _countNewSmSeatsRequiredQuery;
     private readonly IUpdateSecretsManagerSubscriptionCommand _updateSecretsManagerSubscriptionCommand;
+    private readonly IDataProtectorTokenFactory<OrgDeleteTokenable> _orgDeleteTokenDataFactory;
     private readonly IProviderRepository _providerRepository;
     private readonly IOrgUserInviteTokenableFactory _orgUserInviteTokenableFactory;
     private readonly IDataProtectorTokenFactory<OrgUserInviteTokenable> _orgUserInviteTokenDataFactory;
@@ -94,6 +96,7 @@ public class OrganizationService : IOrganizationService
         IOrgUserInviteTokenableFactory orgUserInviteTokenableFactory,
         IDataProtectorTokenFactory<OrgUserInviteTokenable> orgUserInviteTokenDataFactory,
         IUpdateSecretsManagerSubscriptionCommand updateSecretsManagerSubscriptionCommand,
+        IDataProtectorTokenFactory<OrgDeleteTokenable> orgDeleteTokenDataFactory,
         IProviderRepository providerRepository,
         IFeatureService featureService)
     {
@@ -123,6 +126,7 @@ public class OrganizationService : IOrganizationService
         _providerUserRepository = providerUserRepository;
         _countNewSmSeatsRequiredQuery = countNewSmSeatsRequiredQuery;
         _updateSecretsManagerSubscriptionCommand = updateSecretsManagerSubscriptionCommand;
+        _orgDeleteTokenDataFactory = orgDeleteTokenDataFactory;
         _providerRepository = providerRepository;
         _orgUserInviteTokenableFactory = orgUserInviteTokenableFactory;
         _orgUserInviteTokenDataFactory = orgUserInviteTokenDataFactory;
@@ -811,6 +815,23 @@ public class OrganizationService : IOrganizationService
         }
     }
 
+    public async Task InitiateDeleteAsync(Organization organization, string orgAdminEmail)
+    {
+        var orgAdmin = await _userRepository.GetByEmailAsync(orgAdminEmail);
+        if (orgAdmin == null)
+        {
+            throw new BadRequestException("Org admin not found.");
+        }
+        var orgAdminOrgUser = await _organizationUserRepository.GetDetailsByUserAsync(orgAdmin.Id, organization.Id);
+        if (orgAdminOrgUser == null || orgAdminOrgUser.Status != OrganizationUserStatusType.Confirmed ||
+            (orgAdminOrgUser.Type != OrganizationUserType.Admin && orgAdminOrgUser.Type != OrganizationUserType.Owner))
+        {
+            throw new BadRequestException("Org admin not found.");
+        }
+        var token = _orgDeleteTokenDataFactory.Protect(new OrgDeleteTokenable(organization, 1));
+        await _mailService.SendInitiateDeleteOrganzationEmailAsync(orgAdminEmail, organization, token);
+    }
+
     public async Task DeleteAsync(Organization organization)
     {
         await ValidateDeleteOrganizationAsync(organization);

src/Core/MailTemplates/Handlebars/InitiateDeleteOrganzation.html.hbs

@@ -0,0 +1,39 @@
+{{#>FullHtmlLayout}}
+<table width="100%" cellpadding="0" cellspacing="0" style="margin: 0; box-sizing: border-box; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">
+    <tr style="margin: 0; box-sizing: border-box; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">
+        <td class="content-block" style="font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; margin: 0; -webkit-font-smoothing: antialiased; padding: 0 0 10px; -webkit-text-size-adjust: none; text-align: left;" valign="top" align="center">
+            We recently received your request to permanently delete the following Bitwarden organization:
+        </td>
+    </tr>
+    <tr style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">
+        <td class="content-block" style="font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; margin: 0; -webkit-font-smoothing: antialiased; padding: 0 0 10px; -webkit-text-size-adjust: none;" valign="top">
+            <b style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">Name:</b> {{OrganizationName}}<br style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;" />
+            <b style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">ID:</b> {{OrganizationId}}<br style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;" />
+            <b style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">Created:</b> {{OrganizationCreationDate}} at {{OrganizationCreationTime}} {{TimeZone}}<br style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;" />
+            <b style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">Plan:</b> {{OrganizationPlan}}<br style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;" />
+            <b style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">Number of seats:</b> {{OrganizationSeats}}<br style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;" />
+            <b style="margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">Billing email address:</b> {{OrganizationBillingEmail}}
+        </td>
+    </tr>
+    <tr style="margin: 0; box-sizing: border-box; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">
+        <td class="content-block" style="font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; margin: 0; -webkit-font-smoothing: antialiased; padding: 0 0 10px; -webkit-text-size-adjust: none; text-align: left;" valign="top" align="center">
+            Click the link below to delete your Bitwarden organization.
+        </td>
+    </tr>
+    <tr style="margin: 0; box-sizing: border-box; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">
+        <td class="content-block last" style="font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; margin: 0; -webkit-font-smoothing: antialiased; padding: 0; -webkit-text-size-adjust: none; text-align: left;" valign="top" align="center">
+            If you did not request this email to delete your Bitwarden organization, please contact us.
+            <br style="margin: 0; box-sizing: border-box; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;" />
+            <br style="margin: 0; box-sizing: border-box; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;" />
+        </td>
+    </tr>
+    <tr style="margin: 0; box-sizing: border-box; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">
+        <td class="content-block" style="font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; color: #333; line-height: 25px; margin: 0; -webkit-font-smoothing: antialiased; padding: 0 0 10px; -webkit-text-size-adjust: none; text-align: center;" valign="top" align="center">
+            <a href="{{{Url}}}" clicktracking=off target="_blank" style="color: #ffffff; text-decoration: none; text-align: center; cursor: pointer; display: inline-block; border-radius: 5px; background-color: #175DDC; border-color: #175DDC; border-style: solid; border-width: 10px 20px; margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; box-sizing: border-box; font-size: 16px; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;">
+                Delete Your Organization
+            </a>
+            <br style="margin: 0; box-sizing: border-box; color: #333; line-height: 25px; -webkit-font-smoothing: antialiased; -webkit-text-size-adjust: none;" />
+        </td>
+    </tr>
+</table>
+{{/FullHtmlLayout}}

src/Core/MailTemplates/Handlebars/InitiateDeleteOrganzation.text.hbs

@@ -0,0 +1,17 @@
+{{#>BasicTextLayout}}
+We recently received your request to permanently delete the following Bitwarden organization:
+
+- Name: {{OrganizationName}}
+- ID: {{OrganizationId}}
+- Created: {{OrganizationCreationDate}} at {{OrganizationCreationTime}} {{TimeZone}}
+- Plan: {{OrganizationPlan}}
+- Number of seats: {{OrganizationSeats}}
+- Billing email address: {{OrganizationBillingEmail}}
+
+Click the link below to complete the deletion of your organization.
+
+If you did not request this email to delete your Bitwarden organization, please contact us.
+
+{{{Url}}}
+
+{{/BasicTextLayout}}

src/Core/Models/Mail/OrganizationInitiateDeleteModel.cs

@@ -0,0 +1,23 @@
+using Bit.Core.Models.Mail;
+
+namespace Bit.Core.Auth.Models.Mail;
+
+public class OrganizationInitiateDeleteModel : BaseMailModel
+{
+    public string Url => string.Format("{0}/verify-recover-delete-org?orgId={1}&token={2}&name={3}",
+        WebVaultUrl,
+        OrganizationId,
+        Token,
+        OrganizationNameUrlEncoded);
+
+    public string Token { get; set; }
+    public Guid OrganizationId { get; set; }
+    public string OrganizationName { get; set; }
+    public string OrganizationNameUrlEncoded { get; set; }
+    public string OrganizationPlan { get; set; }
+    public string OrganizationSeats { get; set; }
+    public string OrganizationBillingEmail { get; set; }
+    public string OrganizationCreationDate { get; set; }
+    public string OrganizationCreationTime { get; set; }
+    public string TimeZone { get; set; }
+}

src/Core/Services/IMailService.cs

@@ -79,5 +79,6 @@ public interface IMailService
     Task SendTrustedDeviceAdminApprovalEmailAsync(string email, DateTime utcNow, string ip, string deviceTypeAndIdentifier);
     Task SendTrialInitiationEmailAsync(string email);
     Task SendInitiateDeletProviderEmailAsync(string email, Provider provider, string token);
+    Task SendInitiateDeleteOrganzationEmailAsync(string email, Organization organization, string token);
 }
 

src/Core/Services/Implementations/HandlebarsMailService.cs

@@ -1002,6 +1002,30 @@ public class HandlebarsMailService : IMailService
         await _mailDeliveryService.SendEmailAsync(message);
     }
 
+    public async Task SendInitiateDeleteOrganzationEmailAsync(string email, Organization organization, string token)
+    {
+        var message = CreateDefaultMessage("Request to Delete Your Organization", email);
+        var model = new OrganizationInitiateDeleteModel
+        {
+            Token = WebUtility.UrlEncode(token),
+            WebVaultUrl = _globalSettings.BaseServiceUri.VaultWithHash,
+            SiteName = _globalSettings.SiteName,
+            OrganizationId = organization.Id,
+            OrganizationName = CoreHelpers.SanitizeForEmail(organization.DisplayName(), false),
+            OrganizationNameUrlEncoded = WebUtility.UrlEncode(organization.Name),
+            OrganizationBillingEmail = organization.BillingEmail,
+            OrganizationPlan = organization.Plan,
+            OrganizationSeats = organization.Seats.ToString(),
+            OrganizationCreationDate = organization.CreationDate.ToLongDateString(),
+            OrganizationCreationTime = organization.CreationDate.ToShortTimeString(),
+            TimeZone = _utcTimeZoneDisplay,
+        };
+        await AddMessageContentAsync(message, "InitiateDeleteOrganzation", model);
+        message.MetaData.Add("SendGridBypassListManagement", true);
+        message.Category = "InitiateDeleteOrganzation";
+        await _mailDeliveryService.SendEmailAsync(message);
+    }
+
     private static string GetUserIdentifier(string email, string userName)
     {
         return string.IsNullOrEmpty(userName) ? email : CoreHelpers.SanitizeForEmail(userName, false);

src/Core/Services/NoopImplementations/NoopMailService.cs

@@ -270,5 +270,10 @@ public class NoopMailService : IMailService
     }
 
     public Task SendInitiateDeletProviderEmailAsync(string email, Provider provider, string token) => throw new NotImplementedException();
+
+    public Task SendInitiateDeleteOrganzationEmailAsync(string email, Organization organization, string token)
+    {
+        return Task.FromResult(0);
+    }
 }
 

src/Core/Utilities/ModelStateExtensions.cs

@@ -0,0 +1,16 @@
+using Microsoft.AspNetCore.Mvc.ModelBinding;
+
+namespace Bit.Core.Utilities;
+
+public static class ModelStateExtensions
+{
+    public static string GetErrorMessage(this ModelStateDictionary modelState)
+    {
+        var errors = modelState.Values
+            .SelectMany(v => v.Errors)
+            .Select(e => e.ErrorMessage)
+            .ToList();
+
+        return string.Join("; ", errors);
+    }
+}

src/SharedWeb/Utilities/ServiceCollectionExtensions.cs

@@ -150,6 +150,13 @@ public static class ServiceCollectionExtensions
 
     public static void AddTokenizers(this IServiceCollection services)
     {
+        services.AddSingleton<IDataProtectorTokenFactory<OrgDeleteTokenable>>(serviceProvider =>
+            new DataProtectorTokenFactory<OrgDeleteTokenable>(
+                OrgDeleteTokenable.ClearTextPrefix,
+                OrgDeleteTokenable.DataProtectorPurpose,
+                serviceProvider.GetDataProtectionProvider(),
+                serviceProvider.GetRequiredService<ILogger<DataProtectorTokenFactory<OrgDeleteTokenable>>>())
+        );
         services.AddSingleton<IDataProtectorTokenFactory<EmergencyAccessInviteTokenable>>(serviceProvider =>
             new DataProtectorTokenFactory<EmergencyAccessInviteTokenable>(
                 EmergencyAccessInviteTokenable.ClearTextPrefix,

test/Api.Test/AdminConsole/Controllers/OrganizationsControllerTests.cs

@@ -5,6 +5,7 @@ using Bit.Api.Auth.Models.Request.Accounts;
 using Bit.Core;
 using Bit.Core.AdminConsole.Entities;
 using Bit.Core.AdminConsole.Enums.Provider;
+using Bit.Core.AdminConsole.Models.Business.Tokenables;
 using Bit.Core.AdminConsole.OrganizationFeatures.OrganizationApiKeys.Interfaces;
 using Bit.Core.AdminConsole.OrganizationFeatures.OrganizationCollectionEnhancements.Interfaces;
 using Bit.Core.AdminConsole.Repositories;
@@ -20,6 +21,7 @@ using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
+using Bit.Core.Tokens;
 using Bit.Infrastructure.EntityFramework.AdminConsole.Models.Provider;
 using NSubstitute;
 using Xunit;
@@ -47,6 +49,7 @@ public class OrganizationsControllerTests : IDisposable
     private readonly IOrganizationEnableCollectionEnhancementsCommand _organizationEnableCollectionEnhancementsCommand;
     private readonly IProviderRepository _providerRepository;
     private readonly IScaleSeatsCommand _scaleSeatsCommand;
+    private readonly IDataProtectorTokenFactory<OrgDeleteTokenable> _orgDeleteTokenDataFactory;
 
     private readonly OrganizationsController _sut;
 
@@ -70,6 +73,7 @@ public class OrganizationsControllerTests : IDisposable
         _organizationEnableCollectionEnhancementsCommand = Substitute.For<IOrganizationEnableCollectionEnhancementsCommand>();
         _providerRepository = Substitute.For<IProviderRepository>();
         _scaleSeatsCommand = Substitute.For<IScaleSeatsCommand>();
+        _orgDeleteTokenDataFactory = Substitute.For<IDataProtectorTokenFactory<OrgDeleteTokenable>>();
 
         _sut = new OrganizationsController(
             _organizationRepository,
@@ -89,7 +93,8 @@ public class OrganizationsControllerTests : IDisposable
             _pushNotificationService,
             _organizationEnableCollectionEnhancementsCommand,
             _providerRepository,
-            _scaleSeatsCommand);
+            _scaleSeatsCommand,
+            _orgDeleteTokenDataFactory);
     }
 
     public void Dispose()