diff --git a/API/Controllers/SettingsController.cs b/API/Controllers/SettingsController.cs
index ee95328d4..d42b775b2 100644
--- a/API/Controllers/SettingsController.cs
+++ b/API/Controllers/SettingsController.cs
@@ -92,7 +92,7 @@ namespace API.Controllers
 
         [Authorize(Policy = "RequireAdminRole")]
         [HttpPost("test-email-url")]
-        public async Task<ActionResult<bool>> TestEmailServiceUrl(TestEmailDto dto)
+        public async Task<ActionResult<EmailTestResultDto>> TestEmailServiceUrl(TestEmailDto dto)
         {
             return Ok(await _emailService.TestConnectivity(dto.Url));
         }
diff --git a/API/DTOs/Email/EmailTestResultDto.cs b/API/DTOs/Email/EmailTestResultDto.cs
new file mode 100644
index 000000000..a41a6027d
--- /dev/null
+++ b/API/DTOs/Email/EmailTestResultDto.cs
@@ -0,0 +1,10 @@
+namespace API.DTOs.Email;
+
+/// <summary>
+/// Represents if Test Email Service URL was successful or not and if any error occured
+/// </summary>
+public class EmailTestResultDto
+{
+    public bool Successful { get; set; }
+    public string ErrorMessage { get; set; }
+}
diff --git a/API/Services/EmailService.cs b/API/Services/EmailService.cs
index 676e897b3..08d00d29d 100644
--- a/API/Services/EmailService.cs
+++ b/API/Services/EmailService.cs
@@ -3,8 +3,8 @@ using System.Threading.Tasks;
 using API.Data;
 using API.DTOs.Email;
 using API.Entities.Enums;
-using API.Services.Tasks;
 using Flurl.Http;
+using Kavita.Common;
 using Kavita.Common.EnvironmentInfo;
 using Kavita.Common.Helpers;
 using Microsoft.AspNetCore.Http;
@@ -16,9 +16,9 @@ public interface IEmailService
 {
     Task SendConfirmationEmail(ConfirmationEmailDto data);
     Task<bool> CheckIfAccessible(string host);
-    Task SendMigrationEmail(EmailMigrationDto data);
-    Task SendPasswordResetEmail(PasswordResetEmailDto data);
-    Task<bool> TestConnectivity(string emailUrl);
+    Task<bool> SendMigrationEmail(EmailMigrationDto data);
+    Task<bool> SendPasswordResetEmail(PasswordResetEmailDto data);
+    Task<EmailTestResultDto> TestConnectivity(string emailUrl);
 }
 
 public class EmailService : IEmailService
@@ -40,12 +40,23 @@ public class EmailService : IEmailService
             cli.Settings.HttpClientFactory = new UntrustedCertClientFactory());
     }
 
-    public async Task<bool> TestConnectivity(string emailUrl)
+    public async Task<EmailTestResultDto> TestConnectivity(string emailUrl)
     {
-        FlurlHttp.ConfigureClient(emailUrl, cli =>
-            cli.Settings.HttpClientFactory = new UntrustedCertClientFactory());
+        // FlurlHttp.ConfigureClient(emailUrl, cli =>
+        //     cli.Settings.HttpClientFactory = new UntrustedCertClientFactory());
 
-        return await SendEmailWithGet(emailUrl + "/api/email/test");
+        var result = new EmailTestResultDto();
+        try
+        {
+            result.Successful = await SendEmailWithGet(emailUrl + "/api/email/test");
+        }
+        catch (KavitaException ex)
+        {
+            result.Successful = false;
+            result.ErrorMessage = ex.Message;
+        }
+
+        return result;
     }
 
     public async Task SendConfirmationEmail(ConfirmationEmailDto data)
@@ -64,16 +75,16 @@ public class EmailService : IEmailService
         return await SendEmailWithGet(DefaultApiUrl + "/api/email/reachable?host=" + host);
     }
 
-    public async Task SendMigrationEmail(EmailMigrationDto data)
+    public async Task<bool> SendMigrationEmail(EmailMigrationDto data)
     {
         var emailLink = (await _unitOfWork.SettingsRepository.GetSettingAsync(ServerSettingKey.EmailServiceUrl)).Value;
-        await SendEmailWithPost(emailLink + "/api/email/email-migration", data);
+        return await SendEmailWithPost(emailLink + "/api/email/email-migration", data);
     }
 
-    public async Task SendPasswordResetEmail(PasswordResetEmailDto data)
+    public async Task<bool> SendPasswordResetEmail(PasswordResetEmailDto data)
     {
         var emailLink = (await _unitOfWork.SettingsRepository.GetSettingAsync(ServerSettingKey.EmailServiceUrl)).Value;
-        await SendEmailWithPost(emailLink + "/api/email/email-password-reset", data);
+        return await SendEmailWithPost(emailLink + "/api/email/email-password-reset", data);
     }
 
     private static async Task<bool> SendEmailWithGet(string url)
@@ -94,9 +105,9 @@ public class EmailService : IEmailService
                 return true;
             }
         }
-        catch (Exception)
+        catch (Exception ex)
         {
-            return false;
+            throw new KavitaException(ex.Message);
         }
         return false;
     }
diff --git a/UI/Web/src/app/admin/manage-settings/manage-settings.component.ts b/UI/Web/src/app/admin/manage-settings/manage-settings.component.ts
index 7073b15ea..5de5a0ab5 100644
--- a/UI/Web/src/app/admin/manage-settings/manage-settings.component.ts
+++ b/UI/Web/src/app/admin/manage-settings/manage-settings.component.ts
@@ -4,10 +4,11 @@ import { NgbModal } from '@ng-bootstrap/ng-bootstrap';
 import { ToastrService } from 'ngx-toastr';
 import { take } from 'rxjs/operators';
 import { ConfirmService } from 'src/app/shared/confirm.service';
-import { SettingsService } from '../settings.service';
+import { EmailTestResult, SettingsService } from '../settings.service';
 import { DirectoryPickerComponent, DirectoryPickerResult } from '../_modals/directory-picker/directory-picker.component';
 import { ServerSettings } from '../_models/server-settings';
 
+
 @Component({
   selector: 'app-manage-settings',
   templateUrl: './manage-settings.component.html',
@@ -103,11 +104,11 @@ export class ManageSettingsComponent implements OnInit {
   }
 
   testEmailServiceUrl() {
-    this.settingsService.testEmailServerSettings(this.settingsForm.get('emailServiceUrl')?.value || '').pipe(take(1)).subscribe(async (successful: boolean) => {
-      if (successful) {
+    this.settingsService.testEmailServerSettings(this.settingsForm.get('emailServiceUrl')?.value || '').pipe(take(1)).subscribe(async (result: EmailTestResult) => {
+      if (result.successful) {
         this.toastr.success('Email Service Url validated');
       } else {
-        this.toastr.error('Email Service Url did not respond');
+        this.toastr.error('Email Service Url did not respond. ' + result.errorMessage);
       }
       
     }, (err: any) => {
diff --git a/UI/Web/src/app/admin/settings.service.ts b/UI/Web/src/app/admin/settings.service.ts
index 01b7da5f1..ab29e4f86 100644
--- a/UI/Web/src/app/admin/settings.service.ts
+++ b/UI/Web/src/app/admin/settings.service.ts
@@ -1,9 +1,16 @@
 import { HttpClient } from '@angular/common/http';
 import { Injectable } from '@angular/core';
-import { map } from 'rxjs/operators';
 import { environment } from 'src/environments/environment';
 import { ServerSettings } from './_models/server-settings';
 
+/**
+ * Used only for the Test Email Service call
+ */
+export interface EmailTestResult {
+  successful: boolean;
+  errorMessage: string;
+}
+
 @Injectable({
   providedIn: 'root'
 })
@@ -30,7 +37,7 @@ export class SettingsService {
   }
 
   testEmailServerSettings(emailUrl: string) {
-    return this.http.post<boolean>(this.baseUrl + 'settings/test-email-url', {url: emailUrl}, {responseType: 'text' as 'json'});
+    return this.http.post<EmailTestResult>(this.baseUrl + 'settings/test-email-url', {url: emailUrl});
   }
 
   getTaskFrequencies() {