diff --git a/src/Managing.Api/Controllers/LlmController.cs b/src/Managing.Api/Controllers/LlmController.cs
index 4a3b5e92..f6f483af 100644
--- a/src/Managing.Api/Controllers/LlmController.cs
+++ b/src/Managing.Api/Controllers/LlmController.cs
@@ -96,6 +96,7 @@ public class LlmController : BaseController
             int maxIterations = DetermineMaxIterations(request);
             int iteration = 0;
             LlmChatResponse? finalResponse = null;
+            const int DelayBetweenIterationsMs = 500; // 500ms delay between iterations to avoid rate limits
 
             while (iteration < maxIterations)
             {
@@ -103,6 +104,15 @@ public class LlmController : BaseController
                 _logger.LogInformation("LLM chat iteration {Iteration}/{MaxIterations} for user {UserId}",
                     iteration, maxIterations, user.Id);
 
+                // Add delay between iterations to avoid rapid bursts and rate limiting
+                // Skip delay on first iteration
+                if (iteration > 1)
+                {
+                    _logger.LogDebug("Waiting {DelayMs}ms before iteration {Iteration} to avoid rate limits",
+                        DelayBetweenIterationsMs, iteration);
+                    await Task.Delay(DelayBetweenIterationsMs);
+                }
+
                 // Trim context if conversation is getting too long
                 TrimConversationContext(request);
 
diff --git a/src/Managing.Application/LLM/Providers/GeminiProvider.cs b/src/Managing.Application/LLM/Providers/GeminiProvider.cs
index b8080de6..00c39952 100644
--- a/src/Managing.Application/LLM/Providers/GeminiProvider.cs
+++ b/src/Managing.Application/LLM/Providers/GeminiProvider.cs
@@ -1,13 +1,16 @@
+using System.Net;
 using System.Net.Http.Json;
 using System.Text.Json;
 using System.Text.Json.Serialization;
 using Managing.Application.Abstractions.Services;
 using Microsoft.Extensions.Logging;
+using Polly;
+using Polly.Retry;
 
 namespace Managing.Application.LLM.Providers;
 
 /// <summary>
-/// Google Gemini API provider
+/// Google Gemini API provider with retry logic and rate limit handling
 /// </summary>
 public class GeminiProvider : ILlmProvider
 {
@@ -15,8 +18,11 @@ public class GeminiProvider : ILlmProvider
     private readonly string _defaultModel;
     private readonly HttpClient _httpClient;
     private readonly ILogger _logger;
+    private readonly IAsyncPolicy<HttpResponseMessage> _retryPolicy;
     private const string BaseUrl = "https://generativelanguage.googleapis.com/v1beta";
     private const string FallbackModel = "gemini-2.0-flash-exp";
+    private const int MaxRetryAttempts = 3;
+    private const int BaseRetryDelayMs = 2000; // 2 seconds base delay
 
     public string Name => "gemini";
 
@@ -26,6 +32,51 @@ public class GeminiProvider : ILlmProvider
         _defaultModel = defaultModel ?? FallbackModel;
         _httpClient = httpClientFactory?.CreateClient() ?? new HttpClient();
         _logger = logger;
+
+        // Configure retry policy with exponential backoff and Retry-After header support
+        _retryPolicy = Policy
+            .Handle<HttpRequestException>()
+            .Or<TaskCanceledException>()
+            .Or<TimeoutException>()
+            .OrResult<HttpResponseMessage>(r => !r.IsSuccessStatusCode && IsRetryableStatusCode(r.StatusCode))
+            .WaitAndRetryAsync(
+                retryCount: MaxRetryAttempts,
+                sleepDurationProvider: (retryAttempt, result, context) =>
+                {
+                    // Check if response has Retry-After header (for 429 errors)
+                    if (result.Result?.StatusCode == HttpStatusCode.TooManyRequests)
+                    {
+                        var retryAfter = ParseRetryAfterHeader(result.Result);
+                        if (retryAfter.HasValue)
+                        {
+                            _logger.LogInformation(
+                                "Rate limited (429). Respecting Retry-After header: {RetryAfterSeconds}s",
+                                retryAfter.Value.TotalSeconds);
+                            return retryAfter.Value;
+                        }
+                    }
+
+                    // Exponential backoff with jitter: baseDelay * 2^(retryAttempt-1) + random jitter
+                    var exponentialDelay = BaseRetryDelayMs * Math.Pow(2, retryAttempt - 1);
+                    var jitter = new Random().Next(0, BaseRetryDelayMs / 4);
+                    var delay = TimeSpan.FromMilliseconds(exponentialDelay + jitter);
+
+                    _logger.LogInformation(
+                        "Retrying after exponential backoff: {DelayMs}ms (attempt {Attempt}/{MaxAttempts})",
+                        delay.TotalMilliseconds, retryAttempt, MaxRetryAttempts + 1);
+
+                    return delay;
+                },
+                onRetry: (outcome, timespan, retryCount, context) =>
+                {
+                    var exception = outcome.Exception;
+                    var response = outcome.Result;
+                    var errorMessage = exception?.Message ?? $"HTTP {response?.StatusCode}";
+
+                    _logger.LogWarning(
+                        "Gemini API request failed (attempt {RetryCount}/{MaxRetries}): {Error}. Retrying in {Delay}ms",
+                        retryCount, MaxRetryAttempts + 1, errorMessage, timespan.TotalMilliseconds);
+                });
     }
 
     public async Task<LlmChatResponse> ChatAsync(LlmChatRequest request)
@@ -40,12 +91,16 @@ public class GeminiProvider : ILlmProvider
             DefaultIgnoreCondition = JsonIgnoreCondition.WhenWritingNull
         };
 
-        var response = await _httpClient.PostAsJsonAsync(url, geminiRequest, jsonOptions);
+        // Execute request with retry policy
+        var response = await _retryPolicy.ExecuteAsync(async () =>
+        {
+            return await _httpClient.PostAsJsonAsync(url, geminiRequest, jsonOptions);
+        });
 
         if (!response.IsSuccessStatusCode)
         {
             var errorContent = await response.Content.ReadAsStringAsync();
-            _logger.LogError("Gemini API error: {StatusCode} - {Error}", response.StatusCode, errorContent);
+            _logger.LogError("Gemini API error after retries: {StatusCode} - {Error}", response.StatusCode, errorContent);
             throw new HttpRequestException($"Gemini API error: {response.StatusCode} - {errorContent}");
         }
 
@@ -53,6 +108,49 @@ public class GeminiProvider : ILlmProvider
         return ConvertFromGeminiResponse(geminiResponse!);
     }
 
+    /// <summary>
+    /// Checks if an HTTP status code is retryable
+    /// </summary>
+    private static bool IsRetryableStatusCode(HttpStatusCode statusCode)
+    {
+        return statusCode == HttpStatusCode.RequestTimeout ||
+               statusCode == HttpStatusCode.TooManyRequests ||
+               statusCode == HttpStatusCode.InternalServerError ||
+               statusCode == HttpStatusCode.BadGateway ||
+               statusCode == HttpStatusCode.ServiceUnavailable ||
+               statusCode == HttpStatusCode.GatewayTimeout;
+    }
+
+    /// <summary>
+    /// Parses the Retry-After header from HTTP response
+    /// Supports both seconds (integer) and HTTP-date formats
+    /// </summary>
+    private static TimeSpan? ParseRetryAfterHeader(HttpResponseMessage response)
+    {
+        if (!response.Headers.Contains("Retry-After"))
+            return null;
+
+        var retryAfterValues = response.Headers.GetValues("Retry-After");
+        var retryAfterValue = retryAfterValues.FirstOrDefault();
+        if (string.IsNullOrWhiteSpace(retryAfterValue))
+            return null;
+
+        // Try parsing as seconds (integer)
+        if (int.TryParse(retryAfterValue, out var seconds))
+        {
+            return TimeSpan.FromSeconds(seconds);
+        }
+
+        // Try parsing as HTTP-date (RFC 7231)
+        if (DateTime.TryParse(retryAfterValue, out var retryDate))
+        {
+            var delay = retryDate - DateTime.UtcNow;
+            return delay.TotalSeconds > 0 ? delay : null;
+        }
+
+        return null;
+    }
+
     private object ConvertToGeminiRequest(LlmChatRequest request)
     {
         var contents = request.Messages