diff --git a/src/Core/Models/Stripe/StripeInvoiceListOptions.cs b/src/Core/Models/Stripe/StripeInvoiceListOptions.cs
new file mode 100644
index 0000000000..bcffc738da
--- /dev/null
+++ b/src/Core/Models/Stripe/StripeInvoiceListOptions.cs
@@ -0,0 +1,27 @@
+using Stripe;
+
+namespace Bit.Core.Models.BitStripe;
+
+/// <summary>
+/// A model derived from the Stripe <see cref="InvoiceListOptions"/> class that includes a flag used to
+/// retrieve all invoices from the Stripe API rather than a limited set.
+/// </summary>
+public class StripeInvoiceListOptions : InvoiceListOptions
+{
+    public bool SelectAll { get; set; }
+
+    public InvoiceListOptions ToInvoiceListOptions()
+    {
+        var options = (InvoiceListOptions)this;
+
+        if (!SelectAll)
+        {
+            return options;
+        }
+
+        options.EndingBefore = null;
+        options.StartingAfter = null;
+
+        return options;
+    }
+}
diff --git a/src/Core/Services/IStripeAdapter.cs b/src/Core/Services/IStripeAdapter.cs
index 4f1cdd37eb..f79cc1200e 100644
--- a/src/Core/Services/IStripeAdapter.cs
+++ b/src/Core/Services/IStripeAdapter.cs
@@ -18,7 +18,7 @@ public interface IStripeAdapter
     Task<Stripe.Invoice> InvoiceCreateAsync(Stripe.InvoiceCreateOptions options);
     Task<Stripe.InvoiceItem> InvoiceItemCreateAsync(Stripe.InvoiceItemCreateOptions options);
     Task<Stripe.Invoice> InvoiceGetAsync(string id, Stripe.InvoiceGetOptions options);
-    Task<Stripe.StripeList<Stripe.Invoice>> InvoiceListAsync(Stripe.InvoiceListOptions options);
+    Task<List<Stripe.Invoice>> InvoiceListAsync(StripeInvoiceListOptions options);
     IEnumerable<InvoiceItem> InvoiceItemListAsync(InvoiceItemListOptions options);
     Task<Stripe.Invoice> InvoiceUpdateAsync(string id, Stripe.InvoiceUpdateOptions options);
     Task<Stripe.Invoice> InvoiceFinalizeInvoiceAsync(string id, Stripe.InvoiceFinalizeOptions options);
diff --git a/src/Core/Services/Implementations/StripeAdapter.cs b/src/Core/Services/Implementations/StripeAdapter.cs
index 478d092fdc..28dd35034c 100644
--- a/src/Core/Services/Implementations/StripeAdapter.cs
+++ b/src/Core/Services/Implementations/StripeAdapter.cs
@@ -97,9 +97,23 @@ public class StripeAdapter : IStripeAdapter
         return _invoiceService.GetAsync(id, options);
     }
 
-    public Task<Stripe.StripeList<Stripe.Invoice>> InvoiceListAsync(Stripe.InvoiceListOptions options)
+    public async Task<List<Stripe.Invoice>> InvoiceListAsync(StripeInvoiceListOptions options)
     {
-        return _invoiceService.ListAsync(options);
+        if (!options.SelectAll)
+        {
+            return (await _invoiceService.ListAsync(options.ToInvoiceListOptions())).Data;
+        }
+
+        options.Limit = 100;
+
+        var invoices = new List<Stripe.Invoice>();
+
+        await foreach (var invoice in _invoiceService.ListAutoPagingAsync(options.ToInvoiceListOptions()))
+        {
+            invoices.Add(invoice);
+        }
+
+        return invoices;
     }
 
     public IEnumerable<InvoiceItem> InvoiceItemListAsync(InvoiceItemListOptions options)
diff --git a/src/Core/Services/Implementations/StripePaymentService.cs b/src/Core/Services/Implementations/StripePaymentService.cs
index 214b2bff10..67de73a188 100644
--- a/src/Core/Services/Implementations/StripePaymentService.cs
+++ b/src/Core/Services/Implementations/StripePaymentService.cs
@@ -2,6 +2,7 @@
 using Bit.Core.Entities;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
+using Bit.Core.Models.BitStripe;
 using Bit.Core.Models.Business;
 using Bit.Core.Repositories;
 using Bit.Core.Settings;
@@ -668,7 +669,7 @@ public class StripePaymentService : IPaymentService
 
             if (!stripePaymentMethod && subInvoiceMetadata.Any())
             {
-                var invoices = await _stripeAdapter.InvoiceListAsync(new Stripe.InvoiceListOptions
+                var invoices = await _stripeAdapter.InvoiceListAsync(new StripeInvoiceListOptions
                 {
                     Subscription = subscription.Id
                 });
@@ -2138,15 +2139,26 @@ public class StripePaymentService : IPaymentService
             return null;
         }
 
-        var invoices = await _stripeAdapter.InvoiceListAsync(new Stripe.InvoiceListOptions
+        var options = new StripeInvoiceListOptions
         {
             Customer = customer.Id,
-            Limit = 50
-        });
+            SelectAll = true
+        };
 
-        return invoices.Data.Where(i => i.Status != "void" && i.Status != "draft")
-            .OrderByDescending(i => i.Created).Select(i => new BillingInfo.BillingInvoice(i));
+        try
+        {
+            var invoices = await _stripeAdapter.InvoiceListAsync(options);
 
+            return invoices
+                .Where(invoice => invoice.Status != "void" && invoice.Status != "draft")
+                .OrderByDescending(invoice => invoice.Created)
+                .Select(invoice => new BillingInfo.BillingInvoice(invoice));
+        }
+        catch (Stripe.StripeException exception)
+        {
+            _logger.LogError(exception, "An error occurred while listing Stripe invoices");
+            throw new GatewayException("Failed to retrieve current invoices", exception);
+        }
     }
 
     // We are taking only first 30 characters of the SubscriberName because stripe provide