diff --git a/JobTrackerApi.Tests/GmailControllerTests.cs b/JobTrackerApi.Tests/GmailControllerTests.cs
index e3fab2d..353dfef 100644
--- a/JobTrackerApi.Tests/GmailControllerTests.cs
+++ b/JobTrackerApi.Tests/GmailControllerTests.cs
@@ -498,6 +498,14 @@ public sealed class GmailControllerTests
         await db.SaveChangesAsync();
 
         var gmail = new Mock<IGmailOAuthService>();
+        gmail.Setup(service => service.GetConnectionAsync("user-1", It.IsAny<CancellationToken>()))
+            .ReturnsAsync(new GmailConnection
+            {
+                OwnerUserId = "user-1",
+                GmailAddress = "user@example.test",
+                ConnectedAt = DateTimeOffset.UtcNow.AddDays(-1),
+                Scope = "gmail.readonly"
+            });
         gmail.Setup(service => service.ListJobCandidateMessagesAsync("user-1", It.IsAny<IEnumerable<string>>(), 6, It.IsAny<CancellationToken>()))
             .ReturnsAsync(new[]
             {
diff --git a/JobTrackerApi/Controllers/GmailController.cs b/JobTrackerApi/Controllers/GmailController.cs
index 1bc9a9f..9a7c16b 100644
--- a/JobTrackerApi/Controllers/GmailController.cs
+++ b/JobTrackerApi/Controllers/GmailController.cs
@@ -239,6 +239,10 @@ public sealed class GmailController : ControllerBase
         CancellationToken cancellationToken = default)
     {
         var ownerUserId = GetRequiredOwnerUserId();
+        if (await GetOwnerGmailConnectionAsync(ownerUserId, cancellationToken) is null)
+        {
+            return GmailNotConnectedResult();
+        }
         var jobs = await _db.JobApplications
             .Where(x => x.OwnerUserId == ownerUserId && !x.IsDeleted)
             .Include(x => x.Company)
@@ -426,6 +430,10 @@ public sealed class GmailController : ControllerBase
     public async Task<ActionResult<GmailManualSyncResultDto>> ManualSync([FromBody] GmailManualSyncRequest? request, CancellationToken cancellationToken)
     {
         var ownerUserId = GetRequiredOwnerUserId();
+        if (await GetOwnerGmailConnectionAsync(ownerUserId, cancellationToken) is null)
+        {
+            return GmailNotConnectedResult();
+        }
         var jobs = await _db.JobApplications
             .Where(x => x.OwnerUserId == ownerUserId && !x.IsDeleted)
             .Include(x => x.Company)
@@ -552,6 +560,10 @@ public sealed class GmailController : ControllerBase
     public async Task<ActionResult<GmailSuggestedJobsResponseDto>> SuggestedJobs(CancellationToken cancellationToken)
     {
         var ownerUserId = GetRequiredOwnerUserId();
+        if (await GetOwnerGmailConnectionAsync(ownerUserId, cancellationToken) is null)
+        {
+            return GmailNotConnectedResult();
+        }
         var reviewThreads = await ReviewCandidates(null, 6, cancellationToken);
         if (reviewThreads.Result is not OkObjectResult ok || ok.Value is not GmailReviewQueueResponseDto payload)
         {
@@ -1084,6 +1096,20 @@ public sealed class GmailController : ControllerBase
             ?? throw new InvalidOperationException("Authenticated user id is missing.");
     }
 
+    private async Task<GmailConnection?> GetOwnerGmailConnectionAsync(string ownerUserId, CancellationToken cancellationToken)
+    {
+        return await _gmail.GetConnectionAsync(ownerUserId, cancellationToken);
+    }
+
+    private ActionResult GmailNotConnectedResult()
+    {
+        return Conflict(new
+        {
+            code = "gmail_not_connected",
+            message = "Connect Gmail before using the Gmail review queue.",
+        });
+    }
+
     private string GetRedirectUri()
     {
         var configured = (_cfg["Google:GmailRedirectUri"] ?? _cfg["Google:RedirectUri"] ?? "").Trim();
diff --git a/JobTrackerApi/Services/SummarizerService.cs b/JobTrackerApi/Services/SummarizerService.cs
index 1ae180c..76d8070 100644
--- a/JobTrackerApi/Services/SummarizerService.cs
+++ b/JobTrackerApi/Services/SummarizerService.cs
@@ -75,6 +75,7 @@ namespace JobTrackerApi.Services
 
     public class SummarizerService : ISummarizerService
     {
+        private const int AiSummarizeMaxInputChars = 20000;
         private readonly IHttpClientFactory _httpFactory;
         private readonly IMemoryCache _cache;
         private readonly object _metricsLock = new();
@@ -119,10 +120,27 @@ namespace JobTrackerApi.Services
         public Task<string?> SummarizeSectionAsync(string instruction, string text, int maxLength = 180, int minLength = 40)
         {
             if (string.IsNullOrWhiteSpace(instruction) || string.IsNullOrWhiteSpace(text)) return Task.FromResult<string?>(null);
-            var composed = $"{instruction.Trim()}\n\n{text.Trim()}";
+            var composed = ComposeBoundedPrompt(instruction.Trim(), text.Trim());
             return SummarizeCoreAsync(composed, maxLength, minLength);
         }
 
+        private static string ComposeBoundedPrompt(string instruction, string text)
+        {
+            var prefix = $"{instruction}\n\n";
+            if (prefix.Length >= AiSummarizeMaxInputChars)
+            {
+                return prefix[..AiSummarizeMaxInputChars];
+            }
+
+            var remaining = AiSummarizeMaxInputChars - prefix.Length;
+            if (text.Length <= remaining)
+            {
+                return prefix + text;
+            }
+
+            return prefix + text[..remaining];
+        }
+
         private async Task<string?> SummarizeCoreAsync(string text, int maxLength, int minLength)
         {
             var key = BuildCacheKey(text, maxLength, minLength);
@@ -151,7 +169,17 @@ namespace JobTrackerApi.Services
                 var res = await client.PostAsync("/summarize", content);
                 sw.Stop();
                 Interlocked.Add(ref _totalLatencyTicks, sw.ElapsedTicks);
-                if (!res.IsSuccessStatusCode) return null;
+                if (!res.IsSuccessStatusCode)
+                {
+                    var errorBody = await res.Content.ReadAsStringAsync();
+                    Interlocked.Increment(ref _failures);
+                    lock (_metricsLock)
+                    {
+                        _lastFailureAt = DateTimeOffset.UtcNow;
+                        _lastError = $"AI summarize returned {(int)res.StatusCode}: {errorBody}";
+                    }
+                    return null;
+                }
 
                 using var stream = await res.Content.ReadAsStreamAsync();
                 using var doc = await JsonDocument.ParseAsync(stream);