diff --git a/WhatsNew.Cli/Program.cs b/WhatsNew.Cli/Program.cs
index bd1e2b80..a1e50ed1 100644
--- a/WhatsNew.Cli/Program.cs
+++ b/WhatsNew.Cli/Program.cs
@@ -69,6 +69,16 @@ public static async Task Main(
             Console.WriteLine($"Error message: {ex.Message}");
             return;
         }
+
+        Console.WriteLine(whatsNewConfig.LogConfigSettings());
+        if (savefile is not null)
+        {
+            Console.WriteLine($"Writing output to {savefile}");
+        } else
+        {
+            Console.WriteLine($"Writing output to {whatsNewConfig.SaveDir}");
+        }
+
         var pageGenService = new PageGenerationService(whatsNewConfig);
 
         await pageGenService.WriteMarkdownFile(savefile);
diff --git a/WhatsNew.Infrastructure/Models/WhatsNewConfiguration.cs b/WhatsNew.Infrastructure/Models/WhatsNewConfiguration.cs
index 940fa67d..c0f300a4 100644
--- a/WhatsNew.Infrastructure/Models/WhatsNewConfiguration.cs
+++ b/WhatsNew.Infrastructure/Models/WhatsNewConfiguration.cs
@@ -1,6 +1,7 @@
 using DotNetDocs.Tools.GitHubCommunications;
 using DotNetDocs.Tools.Utility;
 using Microsoft.DotnetOrg.Ospo;
+using System.Text;
 
 namespace WhatsNew.Infrastructure.Models;
 
@@ -53,4 +54,17 @@ public class WhatsNewConfiguration
     /// This is the client that makes queries to the Microsoft OSPO office API.
     /// </summary>
     public OspoClient OspoClient { get; set; } = null!;
+
+    public string? LogConfigSettings()
+    {
+        StringBuilder output = new ();
+        output.AppendLine($"Repository: {Repository.Owner}/{Repository.Name}");
+        output.AppendLine($"Branch: {Repository.Branch}");
+        output.AppendLine($"DocSetProductName: {Repository.DocSetProductName}");
+        output.AppendLine($"RootDirectory: {Repository.RootDirectory}");
+        output.AppendLine($"DateRange: {DateRange.StartDate:D} - {DateRange.EndDate:D}");
+        output.AppendLine($"MarkdownFileName: {MarkdownFileName}");
+        output.AppendLine($"PathToRepoRoot: {PathToRepoRoot}");
+        return output.ToString();
+    }
 }
diff --git a/WhatsNew.Infrastructure/Services/PageGenerationService.cs b/WhatsNew.Infrastructure/Services/PageGenerationService.cs
index 36064e37..7077e490 100644
--- a/WhatsNew.Infrastructure/Services/PageGenerationService.cs
+++ b/WhatsNew.Infrastructure/Services/PageGenerationService.cs
@@ -40,7 +40,21 @@ public PageGenerationService(WhatsNewConfiguration configuration) =>
     /// </summary>
     public async Task WriteMarkdownFile(string? existingMarkdownFile= null)
     {
-        await ProcessPullRequests();
+        var totalPRs = await ProcessPullRequests();
+
+        if (totalPRs == 0)
+        {
+            var color = Console.ForegroundColor;
+            Console.ForegroundColor = ConsoleColor.Red;
+            Console.WriteLine("No PRs found.");
+            Console.WriteLine("This is likely a problem with one of:");
+            Console.WriteLine("\t- the date range");
+            Console.WriteLine("\t- the required label");
+            Console.WriteLine("\t- GitHub permissions");
+            Console.WriteLine("Exiting.");
+            Console.ForegroundColor = color;
+            return;
+        }
 
         if (string.IsNullOrWhiteSpace(existingMarkdownFile))
         {
@@ -150,7 +164,6 @@ private async Task WriteNewDocInformation(TextWriter stream, bool singleFile)
         var allDocs = from change in _majorChanges
                       from area in repo.Areas
                       where change.Value.Heading == area.Heading
-                      orderby area.Heading
                       group change by area.Heading into headingGroup
                       select headingGroup;
 
@@ -158,15 +171,23 @@ group change by area.Heading into headingGroup
                                     where area.Names.FirstOrDefault() == "."
                                     select area.Heading).FirstOrDefault();
 
-        foreach (var docArea in allDocs)
+        foreach(var area in repo.Areas)
         {
-            var areaHeading = docArea.Key;
-            var isRootDirectoryArea = areaHeading == rootDirectoryHeading;
-
             // Don't write anything for blank areas.
-            if (areaHeading is null)
+            if (area is null)
                 continue;
-            await stream.WriteLineAsync($"{(singleFile ? "###" : "##")} {areaHeading}");
+            var docArea = allDocs.FirstOrDefault(da => da.Key == area.Heading);
+            if (docArea is null)
+            {
+                Console.WriteLine($"No changes found for {area.Heading}");
+                continue;
+            } else
+            {
+                Console.WriteLine($"Writing changes for {area.Heading}");
+            }
+            var isRootDirectoryArea = area.Heading == rootDirectoryHeading;
+
+            await stream.WriteLineAsync($"{(singleFile ? "###" : "##")} {area.Heading}");
             await stream.WriteLineAsync();
 
             writeDocNodes(true);
@@ -274,6 +295,7 @@ void writeDocNodes(bool isNew)
 
     private async Task WriteContributorInformation(TextWriter stream)
     {
+        Console.WriteLine("Writing contributors");
         var allContributors = from c in _contributors
                               orderby c.login
                               group c by (c.login, c.name) into stats
@@ -301,23 +323,24 @@ group c by (c.login, c.name) into stats
         }
     }
 
-    private async Task ProcessPullRequests()
+    private async Task<int> ProcessPullRequests()
     {
         var repo = _configuration.Repository;
         var client = _configuration.GitHubClient;
         var ospoClient = _configuration.OspoClient;
 
-        await processPRs();
+        var totalPRs = await processPRs();
 
         // If processing a private repo, fetch the PRs & community contributors from
         // the accompanying public repo. Merge private results with public results.
         if (repo.IsPrivateRepo)
         {
             repo.Name = repo.Name.Replace(PrivateRepoNameSuffix, string.Empty);
-            await processPRs();
+            totalPRs += await processPRs();
         }
+        return totalPRs;
 
-        async Task processPRs()
+        async Task<int> processPRs()
         {
             Console.ForegroundColor = ConsoleColor.DarkMagenta;
             Console.WriteLine($"== {repo.Owner}/{repo.Name} ({repo.Branch}) ==", Console.ForegroundColor);
@@ -328,8 +351,10 @@ async Task processPRs()
                 client, repo.Owner, repo.Name, repo.Branch, repo.InclusionCriteria.Labels, _configuration.DateRange);
             var authorLoginFTECache = new Dictionary<string, bool?>();
 
+            var totalPRs = 0;
             await foreach (var item in query.PerformQuery())
             {
+                totalPRs++;
                 var prNumber = item.Number;
                 Console.WriteLine($"Processing PR {prNumber}");
 
@@ -358,6 +383,7 @@ async Task processPRs()
                 Console.WriteLine($"{index}. {distinctExcludedContributors[index - 1]}");
             }
             Console.WriteLine();
+            return totalPRs;
         }
     }