diff --git a/DiscordChatExporter.Core/Discord/DiscordClient.cs b/DiscordChatExporter.Core/Discord/DiscordClient.cs
index 9ec5b112..5fe033a8 100644
--- a/DiscordChatExporter.Core/Discord/DiscordClient.cs
+++ b/DiscordChatExporter.Core/Discord/DiscordClient.cs
@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.Globalization;
 using System.Linq;
 using System.Net;
 using System.Net.Http;
@@ -35,7 +36,7 @@ public class DiscordClient
         {
             using var request = new HttpRequestMessage(HttpMethod.Get, new Uri(_baseUri, url));
 
-            // Don't validate because token can have invalid characters
+            // Don't validate because token can have special characters
             // https://github.com/Tyrrrz/DiscordChatExporter/issues/828
             request.Headers.TryAddWithoutValidation(
                 "Authorization",
@@ -44,11 +45,32 @@ public class DiscordClient
                     : _token
             );
 
-            return await Http.Client.SendAsync(
+            var response = await Http.Client.SendAsync(
                 request,
                 HttpCompletionOption.ResponseHeadersRead,
                 innerCancellationToken
             );
+
+            // If this was the last request available before hitting the rate limit,
+            // wait out the reset time so that future requests can succeed.
+            // This may add an unnecessary delay in case the user doesn't intend to
+            // make any more requests, but implementing a smarter solution would
+            // require properly keeping track of Discord's global/per-route/per-resource
+            // rate limits and that's not worth the effort.
+            var remainingRequestCount = response
+                .Headers
+                .TryGetValue("X-RateLimit-Remaining")?
+                .Pipe(s => int.Parse(s, CultureInfo.InvariantCulture));
+
+            var resetAfterDelay = response
+                .Headers
+                .TryGetValue("X-RateLimit-Reset-After")?
+                .Pipe(s => TimeSpan.FromSeconds(double.Parse(s, CultureInfo.InvariantCulture)));
+
+            if (remainingRequestCount <= 0 && resetAfterDelay is not null)
+                await Task.Delay(resetAfterDelay.Value + TimeSpan.FromSeconds(1), innerCancellationToken);
+
+            return response;
         }, cancellationToken);
     }
 
diff --git a/DiscordChatExporter.Core/Utils/Extensions/HttpExtensions.cs b/DiscordChatExporter.Core/Utils/Extensions/HttpExtensions.cs
index 0f74ad1a..971a8e34 100644
--- a/DiscordChatExporter.Core/Utils/Extensions/HttpExtensions.cs
+++ b/DiscordChatExporter.Core/Utils/Extensions/HttpExtensions.cs
@@ -4,7 +4,7 @@ namespace DiscordChatExporter.Core.Utils.Extensions;
 
 public static class HttpExtensions
 {
-    public static string? TryGetValue(this HttpContentHeaders headers, string name) =>
+    public static string? TryGetValue(this HttpHeaders headers, string name) =>
         headers.TryGetValues(name, out var values)
             ? string.Concat(values)
             : null;
diff --git a/DiscordChatExporter.Core/Utils/Http.cs b/DiscordChatExporter.Core/Utils/Http.cs
index 77ae52ad..ab25951b 100644
--- a/DiscordChatExporter.Core/Utils/Http.cs
+++ b/DiscordChatExporter.Core/Utils/Http.cs
@@ -39,19 +39,9 @@ public static class Http
                 8,
                 (i, result, _) =>
                 {
-                    // If rate-limited, use retry-after as a guide
-                    if (result.Result?.StatusCode == HttpStatusCode.TooManyRequests)
-                    {
-                        // Only start respecting retry-after after a few attempts, because
-                        // Discord often sends unreasonable (20+ minutes) retry-after
-                        // on the very first request.
-                        if (i > 3)
-                        {
-                            var retryAfterDelay = result.Result.Headers.RetryAfter?.Delta;
-                            if (retryAfterDelay is not null)
-                                return retryAfterDelay.Value + TimeSpan.FromSeconds(1); // margin just in case
-                        }
-                    }
+                    // If rate-limited, use retry-after header as the guide
+                    if (result.Result.Headers.RetryAfter?.Delta is { } retryAfter)
+                        return retryAfter + TimeSpan.FromSeconds(1);
 
                     return TimeSpan.FromSeconds(Math.Pow(2, i) + 1);
                 },