diff --git a/.github/workflows/Build-Test-And-Deploy.yml b/.github/workflows/Build-Test-And-Deploy.yml
index cb441a0b..b888ba0c 100644
--- a/.github/workflows/Build-Test-And-Deploy.yml
+++ b/.github/workflows/Build-Test-And-Deploy.yml
@@ -71,9 +71,6 @@ jobs:
         uses: actions/setup-dotnet@v6
         with:
           global-json-file: global.json
-          source-url: https://pkgs.dev.azure.com/intelliTect/_packaging/EssentialCSharp/nuget/v3/index.json
-        env:
-          NUGET_AUTH_TOKEN: ${{ secrets.AZURE_DEVOPS_PAT }}
 
       - name: Set up dependency caching for faster builds
         uses: actions/cache@v6
@@ -87,11 +84,26 @@ jobs:
             ${{ runner.os }}-nuget-${{ hashFiles('**/packages.lock.json') }}
             ${{ runner.os }}-nuget-
 
+      # Restore against the private content feed so the tests below run against the real content package
+      # (placeholders only mirror its file shapes). This job only runs on push/workflow_dispatch, never for
+      # fork PRs. The credentials exist only for the restore and are removed before any repo code builds or runs.
+      - name: Generate NuGet feed credentials
+        env:
+          NUGET_FEED_TOKEN: ${{ secrets.AZURE_DEVOPS_PAT }}
+        run: |
+          mkdir -p "${HOME}/.nuget/NuGet"
+          bash scripts/nuget/emit-creds-config.sh > "${HOME}/.nuget/NuGet/NuGet.Config"
+          chmod 600 "${HOME}/.nuget/NuGet/NuGet.Config"
+
       - name: Restore with dotnet
-        run: dotnet restore
+        run: dotnet restore -p:AccessToNugetFeed=true
+
+      - name: Remove NuGet feed credentials
+        if: always()
+        run: rm -f "${HOME}/.nuget/NuGet/NuGet.Config"
 
       - name: Build with dotnet
-        run: dotnet build -p:ContinuousIntegrationBuild=True -p:ReleaseDateAttribute=True -p:SkipFrontendBuild=true --configuration Release --no-restore
+        run: dotnet build -p:AccessToNugetFeed=true -p:ContinuousIntegrationBuild=True -p:ReleaseDateAttribute=True -p:SkipFrontendBuild=true --configuration Release --no-restore
 
       - name: Expose GitHub Actions Runtime
         uses: actions/github-script@v9
@@ -332,6 +344,16 @@ jobs:
             --resource-group "$RESOURCEGROUP" \
             --image "${{ vars.DEVCONTAINER_REGISTRY }}/essentialcsharpweb:${{ github.sha }}"
 
+      # Requests real pages, not just /health: content-backed services are built lazily on first page
+      # request, so a bad content file leaves /health green while pages return 500.
+      - name: Smoke test
+        env:
+          CONTAINER_APP_NAME: ${{ vars.CONTAINER_APP_NAME }}
+          RESOURCEGROUP: ${{ vars.RESOURCEGROUP }}
+        run: |
+          FQDN=$(az containerapp show             --name "$CONTAINER_APP_NAME"             --resource-group "$RESOURCEGROUP"             --query "properties.configuration.ingress.fqdn" -o tsv)
+          bash scripts/smoke-test.sh "$FQDN"
+
       - name: Logout of Azure CLI
         if: always()
         uses: azure/CLI@v3
@@ -433,8 +455,7 @@ jobs:
             --name "$CONTAINER_APP_NAME" \
             --resource-group "$RESOURCEGROUP" \
             --query "properties.configuration.ingress.fqdn" -o tsv)
-          # --retry-all-errors ensures HTTP 5xx (cold-start 503s) also trigger retries
-          curl --fail --retry 10 --retry-delay 15 --retry-all-errors --max-time 30 "https://$FQDN/health"
+          bash scripts/smoke-test.sh "$FQDN"
 
       - name: Cancel pending deployment workflow runs
         uses: actions/github-script@v9
diff --git a/EssentialCSharp.Web.Tests/ChapterDescriptionServiceTests.cs b/EssentialCSharp.Web.Tests/ChapterDescriptionServiceTests.cs
index 9ba41312..f35eebb7 100644
--- a/EssentialCSharp.Web.Tests/ChapterDescriptionServiceTests.cs
+++ b/EssentialCSharp.Web.Tests/ChapterDescriptionServiceTests.cs
@@ -39,6 +39,48 @@ public async Task WithoutGeneratedDescriptionsUsesPageHeading()
         await Assert.That(service.GetDescription(CreateMapping("sample", "Sample Heading"))).Contains("Sample Heading");
     }
 
+    // Shape emitted by the content package (a single "Key" per entry).
+    [Test]
+    public async Task SingularKeyEntriesFromContentPackageAreLoaded()
+    {
+        ChapterDescriptionService service = CreateServiceFromJson(
+            """[{"Key":"example-page","Value":"Singular key description."}]""");
+
+        await Assert.That(service.Count).IsEqualTo(1);
+        await Assert.That(service.GetDescription(CreateMapping("EXAMPLE-PAGE", "Examples"))).IsEqualTo("Singular key description.");
+    }
+
+    [Test]
+    [Arguments("""{"Key":"a","Value":"b"}""")]
+    [Arguments("""[null]""")]
+    [Arguments("""[{"Value":"no key"}]""")]
+    [Arguments("""[{"Key":"a"}]""")]
+    [Arguments("""[{"Keys":[""],"Value":"empty key"}]""")]
+    [Arguments("""[{"Keys":"a","Value":"keys is not an array"}]""")]
+    public async Task MalformedDescriptionsFailWithAClearMessage(string json)
+    {
+        await Assert.That(() => CreateServiceFromJson(json))
+            .Throws<InvalidDataException>()
+            .WithMessageContaining("sitemap.descriptions.json");
+    }
+
+    private static ChapterDescriptionService CreateServiceFromJson(string json)
+    {
+        string directory = Path.Combine(Path.GetTempPath(), Guid.NewGuid().ToString());
+        Directory.CreateDirectory(Path.Combine(directory, "Chapters"));
+        try
+        {
+            File.WriteAllText(Path.Combine(directory, "Chapters", "sitemap.descriptions.json"), json);
+            Mock<IWebHostEnvironment> environment = new();
+            environment.SetupGet(e => e.ContentRootPath).Returns(directory);
+            return new ChapterDescriptionService(environment.Object);
+        }
+        finally
+        {
+            Directory.Delete(directory, recursive: true);
+        }
+    }
+
     private static SiteMapping CreateMapping(string key, string heading) =>
         new([key], key, ["Chapters", "01", "Pages", "01.html"], 1, 1, 1,
             "Chapter One", heading, null, 1);
diff --git a/EssentialCSharp.Web.Tests/ContentPackageContractTests.cs b/EssentialCSharp.Web.Tests/ContentPackageContractTests.cs
new file mode 100644
index 00000000..5bd7ee7d
--- /dev/null
+++ b/EssentialCSharp.Web.Tests/ContentPackageContractTests.cs
@@ -0,0 +1,33 @@
+using EssentialCSharp.Web.Services;
+using Microsoft.Extensions.DependencyInjection;
+
+namespace EssentialCSharp.Web.Tests;
+
+/// <summary>
+/// Loads the content files the app actually has on disk through the real services. With
+/// <c>-p:AccessToNugetFeed=true</c> these are the files from the content package; otherwise they are the
+/// placeholders in <c>Placeholders/</c>, which must mirror the package's file shapes. Assertions are
+/// structural only so a failure never prints book content into a public log.
+/// </summary>
+public class ContentPackageContractTests : IntegrationTestBase
+{
+    [Test]
+    public async Task ChapterDescriptionsLoad()
+    {
+        ChapterDescriptionService descriptions = Factory.Inner.Services.GetRequiredService<ChapterDescriptionService>();
+
+        await Assert.That(descriptions.Count).IsGreaterThan(0);
+    }
+
+    [Test]
+    public async Task SiteMapAndGuidelinesLoad()
+    {
+        IServiceProvider services = Factory.Inner.Services;
+
+        using (Assert.Multiple())
+        {
+            await Assert.That(services.GetRequiredService<ISiteMappingService>().SiteMappings).IsNotEmpty();
+            await Assert.That(services.GetRequiredService<IGuidelinesService>().Guidelines).IsNotEmpty();
+        }
+    }
+}
diff --git a/EssentialCSharp.Web.Tests/FunctionalTests.cs b/EssentialCSharp.Web.Tests/FunctionalTests.cs
index 32b785f9..9c111d4a 100644
--- a/EssentialCSharp.Web.Tests/FunctionalTests.cs
+++ b/EssentialCSharp.Web.Tests/FunctionalTests.cs
@@ -55,9 +55,9 @@ public async Task WhenPagesAreAccessed_TheyReturnHtml(string relativeUrl)
     [Arguments("/announcements", "https://essentialcsharp.com/announcements", "announcements")]
     [Arguments("/TermsOfService", "https://essentialcsharp.com/TermsOfService", "terms of service")]
     [Arguments("/mcp-setup", "https://essentialcsharp.com/mcp-setup", "Model Context Protocol")]
-    [Arguments("/introducing-c", "https://essentialcsharp.com/introducing-c", "Introducing C#")]
-    [Arguments("/hello-world", "https://essentialcsharp.com/introducing-c", "Hello")]
-    public async Task PagesHaveOneCanonicalAndPageSpecificDescriptions(string path, string expectedCanonical, string expectedDescription)
+    [Arguments("/introducing-c", "https://essentialcsharp.com/introducing-c", null)]
+    [Arguments("/hello-world", "https://essentialcsharp.com/introducing-c", null)]
+    public async Task PagesHaveOneCanonicalAndPageSpecificDescriptions(string path, string expectedCanonical, string? expectedDescription)
     {
         await using WebApplicationFactory<Program> factory = CreateFactoryWithBaseUrl("https://essentialcsharp.com");
         await AssertPageMetadata(factory, path, expectedCanonical, expectedDescription);
@@ -65,9 +65,9 @@ public async Task PagesHaveOneCanonicalAndPageSpecificDescriptions(string path,
 
     [Test]
     [Arguments("/about", "https://dev.essentialcsharp.com/about", "Learn about Essential C#")]
-    [Arguments("/introducing-c", "https://dev.essentialcsharp.com/introducing-c", "Introducing C#")]
-    [Arguments("/hello-world?rid=abc", "https://dev.essentialcsharp.com/introducing-c", "Hello")]
-    public async Task CanonicalUrlsUseConfiguredDeploymentOrigin(string path, string expectedCanonical, string expectedDescription)
+    [Arguments("/introducing-c", "https://dev.essentialcsharp.com/introducing-c", null)]
+    [Arguments("/hello-world?rid=abc", "https://dev.essentialcsharp.com/introducing-c", null)]
+    public async Task CanonicalUrlsUseConfiguredDeploymentOrigin(string path, string expectedCanonical, string? expectedDescription)
     {
         await using WebApplicationFactory<Program> factory = CreateFactoryWithBaseUrl("https://dev.essentialcsharp.com/");
         await AssertPageMetadata(factory, path, expectedCanonical, expectedDescription);
@@ -77,7 +77,7 @@ private WebApplicationFactory<Program> CreateFactoryWithBaseUrl(string baseUrl)
         Factory.Inner.WithWebHostBuilder(builder => builder.ConfigureServices(services =>
             services.PostConfigure<SiteSettings>(settings => settings.BaseUrl = baseUrl)));
 
-    private static async Task AssertPageMetadata(WebApplicationFactory<Program> factory, string path, string expectedCanonical, string expectedDescription)
+    private static async Task AssertPageMetadata(WebApplicationFactory<Program> factory, string path, string expectedCanonical, string? expectedDescription)
     {
         using HttpClient client = factory.CreateClient(new WebApplicationFactoryClientOptions { AllowAutoRedirect = false });
         using HttpResponseMessage response = await GetFollowingGetRedirectsAsync(client, path);
@@ -92,7 +92,15 @@ private static async Task AssertPageMetadata(WebApplicationFactory<Program> fact
         await Assert.That((head.SelectSingleNode("meta[@property='og:url']") ?? throw new InvalidOperationException("Missing OG URL")).GetAttributeValue("content", "")).IsEqualTo(expectedCanonical);
 
         string description = (head.SelectSingleNode("meta[@name='description']") ?? throw new InvalidOperationException("Missing description")).GetAttributeValue("content", "");
-        await Assert.That(description).Contains(expectedDescription);
+        if (expectedDescription is null)
+        {
+            await Assert.That(description).IsNotEmpty();
+            await Assert.That(description).DoesNotContain("Accelerate your development knowledge");
+        }
+        else
+        {
+            await Assert.That(description).Contains(expectedDescription);
+        }
         await Assert.That((head.SelectNodes("meta[@name='description']") ?? throw new InvalidOperationException("Missing description")).Count).IsEqualTo(1);
         await Assert.That((head.SelectSingleNode("meta[@property='og:description']") ?? throw new InvalidOperationException("Missing OG description")).GetAttributeValue("content", "")).IsEqualTo(description);
         await Assert.That((head.SelectSingleNode("meta[@name='twitter:description']") ?? throw new InvalidOperationException("Missing Twitter description")).GetAttributeValue("content", "")).IsEqualTo(description);
diff --git a/EssentialCSharp.Web.Tests/PlaceholderShapeTests.cs b/EssentialCSharp.Web.Tests/PlaceholderShapeTests.cs
new file mode 100644
index 00000000..e9f44e95
--- /dev/null
+++ b/EssentialCSharp.Web.Tests/PlaceholderShapeTests.cs
@@ -0,0 +1,92 @@
+using System.Text.Json;
+using Microsoft.AspNetCore.Hosting;
+using Microsoft.Extensions.DependencyInjection;
+
+namespace EssentialCSharp.Web.Tests;
+
+/// <summary>
+/// The placeholders in <c>Placeholders/</c> stand in for the content package in PR builds, so they must have
+/// the same JSON shape. When the build uses the real package (<c>-p:AccessToNugetFeed=true</c>) the content
+/// files differ from the placeholders and this fails if the package changed shape. Without the package the
+/// content files are the placeholders, so it passes trivially. Only property names and value kinds are
+/// compared, and failures report only those, so no book content reaches a public log.
+/// </summary>
+public class PlaceholderShapeTests : IntegrationTestBase
+{
+    [Test]
+    [Arguments("Chapters/sitemap.json", "sitemap.json")]
+    [Arguments("Chapters/sitemap.descriptions.json", "sitemap.descriptions.json")]
+    [Arguments("Guidelines/guidelines.json", "guidelines.json")]
+    public async Task PlaceholderMatchesContentShape(string contentPath, string placeholderName)
+    {
+        string root = Factory.Inner.Services.GetRequiredService<IWebHostEnvironment>().ContentRootPath;
+        string placeholderPath = Path.Combine(root, "Placeholders", placeholderName);
+        string actualPath = Path.Combine(root, contentPath);
+
+        Dictionary<string, HashSet<string>> placeholder = ReadShape(placeholderPath);
+        Dictionary<string, HashSet<string>> actual = ReadShape(actualPath);
+
+        List<string> differences = [];
+        foreach (string name in placeholder.Keys.Except(actual.Keys))
+        {
+            differences.Add($"property \"{name}\" is only in the placeholder");
+        }
+        foreach (string name in actual.Keys.Except(placeholder.Keys))
+        {
+            differences.Add($"property \"{name}\" is only in the content package");
+        }
+        foreach (string name in placeholder.Keys.Intersect(actual.Keys))
+        {
+            // Nulls are ignored: optional fields may be null throughout one file and populated in the other.
+            if (placeholder[name].Count > 0 && actual[name].Count > 0 && !placeholder[name].SetEquals(actual[name]))
+            {
+                differences.Add($"property \"{name}\" is {string.Join("/", placeholder[name].Order())} in the placeholder but {string.Join("/", actual[name].Order())} in the content package");
+            }
+        }
+
+        await Assert.That(differences)
+            .IsEmpty()
+            .Because($"Placeholders/{placeholderName} must mirror {contentPath} from the content package: update the placeholder to the package's shape. {string.Join("; ", differences)}");
+    }
+
+    // Maps each property name used by the entries of a JSON array to the non-null value kinds seen for it
+    // (arrays are described by their element kinds, e.g. "Array<String>").
+    private static Dictionary<string, HashSet<string>> ReadShape(string path)
+    {
+        using FileStream stream = File.OpenRead(path);
+        using JsonDocument document = JsonDocument.Parse(stream);
+        if (document.RootElement.ValueKind != JsonValueKind.Array)
+        {
+            throw new InvalidDataException($"Expected a JSON array in {Path.GetFileName(path)}");
+        }
+
+        Dictionary<string, HashSet<string>> shape = [];
+        foreach (JsonElement entry in document.RootElement.EnumerateArray())
+        {
+            if (entry.ValueKind != JsonValueKind.Object)
+            {
+                throw new InvalidDataException($"Expected every entry in {Path.GetFileName(path)} to be an object");
+            }
+
+            foreach (JsonProperty property in entry.EnumerateObject())
+            {
+                if (!shape.TryGetValue(property.Name, out HashSet<string>? kinds))
+                {
+                    shape[property.Name] = kinds = [];
+                }
+
+                if (property.Value.ValueKind != JsonValueKind.Null)
+                {
+                    kinds.Add(Describe(property.Value));
+                }
+            }
+        }
+
+        return shape;
+    }
+
+    private static string Describe(JsonElement value) =>
+        value.ValueKind == JsonValueKind.Array
+            ? $"Array<{string.Join("|", value.EnumerateArray().Select(Describe).Distinct().Order())}>"
+            : value.ValueKind.ToString();
+}
diff --git a/EssentialCSharp.Web/EssentialCSharp.Web.csproj b/EssentialCSharp.Web/EssentialCSharp.Web.csproj
index be1eb33d..9ff05a0c 100644
--- a/EssentialCSharp.Web/EssentialCSharp.Web.csproj
+++ b/EssentialCSharp.Web/EssentialCSharp.Web.csproj
@@ -26,6 +26,7 @@
     <PlaceholderChapterOneHtmlFile Include="$(ProjectDir)/Placeholders/Chapters/01/Pages/*.html" />
     <PlaceholderChapterTwoHtmlFile Include="$(ProjectDir)/Placeholders/Chapters/02/Pages/*.html" />
     <PlaceholderSitemapJsonFile Include="$(ProjectDir)/Placeholders/sitemap.json" />
+    <PlaceholderSitemapDescriptionsJsonFile Include="$(ProjectDir)/Placeholders/sitemap.descriptions.json" />
     <PlaceholderGuidelinesJsonFile Include="$(ProjectDir)/Placeholders/guidelines.json" />
   </ItemGroup>
 
@@ -87,6 +88,7 @@
   </ItemGroup>
   <Target Condition="!$(AccessToNugetFeed)" Name="CopyPlaceholderContent" BeforeTargets="Build">
     <Copy SourceFiles="@(PlaceholderSitemapJsonFile)" DestinationFolder="$(ProjectDir)/Chapters/" SkipUnchangedFiles="true" />
+    <Copy SourceFiles="@(PlaceholderSitemapDescriptionsJsonFile)" DestinationFolder="$(ProjectDir)/Chapters/" SkipUnchangedFiles="true" />
     <Copy SourceFiles="@(PlaceholderGuidelinesJsonFile)" DestinationFolder="$(ProjectDir)/Guidelines/" SkipUnchangedFiles="true" />
     <Copy SourceFiles="@(PlaceholderChapterOneHtmlFile)" DestinationFolder="$(ProjectDir)/Chapters/01/Pages/" SkipUnchangedFiles="true" />
     <Copy SourceFiles="@(PlaceholderChapterTwoHtmlFile)" DestinationFolder="$(ProjectDir)/Chapters/02/Pages/" SkipUnchangedFiles="true" />
diff --git a/EssentialCSharp.Web/Placeholders/sitemap.descriptions.json b/EssentialCSharp.Web/Placeholders/sitemap.descriptions.json
new file mode 100644
index 00000000..914e3273
--- /dev/null
+++ b/EssentialCSharp.Web/Placeholders/sitemap.descriptions.json
@@ -0,0 +1,158 @@
+[
+  {
+    "Key": "introducing-c",
+    "Value": "Placeholder description for Introducing C# in Essential C#."
+  },
+  {
+    "Key": "hello-world",
+    "Value": "Placeholder description for Hello, World in Essential C#."
+  },
+  {
+    "Key": "creating-editing-compiling-and-running-c-source-code",
+    "Value": "Placeholder description for Creating, Editing, Compiling, and Running C# Source Code in Essential C#."
+  },
+  {
+    "Key": "with-dotnet-cli",
+    "Value": "Placeholder description for With Dotnet CLI in Essential C#."
+  },
+  {
+    "Key": "with-visual-studio-2022-windows-or-mac",
+    "Value": "Placeholder description for With Visual Studio 2022 (Windows or Mac) in Essential C#."
+  },
+  {
+    "Key": "understanding-a-project",
+    "Value": "Placeholder description for Understanding a Project in Essential C#."
+  },
+  {
+    "Key": "compilation-and-execution",
+    "Value": "Placeholder description for Compilation and Execution in Essential C#."
+  },
+  {
+    "Key": "essential-c-source-code",
+    "Value": "Placeholder description for Essential C# Source Code in Essential C#."
+  },
+  {
+    "Key": "c-syntax-fundamentals",
+    "Value": "Placeholder description for C# Syntax Fundamentals in Essential C#."
+  },
+  {
+    "Key": "statements-and-statement-delimiters",
+    "Value": "Placeholder description for Statements and Statement Delimiters in Essential C#."
+  },
+  {
+    "Key": "introducing-a-class-and-a-method",
+    "Value": "Placeholder description for Introducing a Class and a Method in Essential C#."
+  },
+  {
+    "Key": "c-keywords",
+    "Value": "Placeholder description for C# Keywords in Essential C#."
+  },
+  {
+    "Key": "identifiers",
+    "Value": "Placeholder description for Identifiers in Essential C#."
+  },
+  {
+    "Key": "type-definition",
+    "Value": "Placeholder description for Type Definition in Essential C#."
+  },
+  {
+    "Key": "main-method",
+    "Value": "Placeholder description for Main Method in Essential C#."
+  },
+  {
+    "Key": "whitespace",
+    "Value": "Placeholder description for Whitespace in Essential C#."
+  },
+  {
+    "Key": "working-with-variables",
+    "Value": "Placeholder description for Working with Variables in Essential C#."
+  },
+  {
+    "Key": "introducing-data-types",
+    "Value": "Placeholder description for Introducing Data Types in Essential C#."
+  },
+  {
+    "Key": "declaring-a-variable",
+    "Value": "Placeholder description for Declaring a Variable in Essential C#."
+  },
+  {
+    "Key": "assigning-a-variable",
+    "Value": "Placeholder description for Assigning a Variable in Essential C#."
+  },
+  {
+    "Key": "using-a-variable",
+    "Value": "Placeholder description for Using a Variable in Essential C#."
+  },
+  {
+    "Key": "console-input-and-output",
+    "Value": "Placeholder description for Console Input and Output in Essential C#."
+  },
+  {
+    "Key": "getting-input-from-the-console",
+    "Value": "Placeholder description for Getting Input from the Console in Essential C#."
+  },
+  {
+    "Key": "writing-output-to-the-console",
+    "Value": "Placeholder description for Writing Output to the Console in Essential C#."
+  },
+  {
+    "Key": "comments",
+    "Value": "Placeholder description for Comments in Essential C#."
+  },
+  {
+    "Key": "debugging",
+    "Value": "Placeholder description for Debugging in Essential C#."
+  },
+  {
+    "Key": "managed-execution-and-the-common-language-infrastructure",
+    "Value": "Placeholder description for Managed Execution and the Common Language Infrastructure in Essential C#."
+  },
+  {
+    "Key": "common-intermediate-language-and-ildasm",
+    "Value": "Placeholder description for Common Intermediate Language and Ildasm in Essential C#."
+  },
+  {
+    "Key": "multiple-net-frameworks",
+    "Value": "Placeholder description for Multiple .NET Frameworks in Essential C#."
+  },
+  {
+    "Key": "application-programming-interface",
+    "Value": "Placeholder description for Application Programming Interface in Essential C#."
+  },
+  {
+    "Key": "c-and-net-versioning",
+    "Value": "Placeholder description for C# and .NET Versioning in Essential C#."
+  },
+  {
+    "Key": "chapter-1-summary",
+    "Value": "Placeholder description for Chapter 1: Summary in Essential C#."
+  },
+  {
+    "Key": "data-types",
+    "Value": "Placeholder description for Data Types in Essential C#."
+  },
+  {
+    "Key": "type-name-forms",
+    "Value": "Placeholder description for Type Name Forms in Essential C#."
+  },
+  {
+    "Key": "fundamental-numeric-types",
+    "Value": "Placeholder description for Fundamental Numeric Types in Essential C#."
+  },
+  {
+    "Key": "integer-types",
+    "Value": "Placeholder description for Integer Types in Essential C#."
+  },
+  {
+    "Key": "floating-point-types-float-double",
+    "Value": "Placeholder description for Floating-Point Types (float, double) in Essential C#."
+  },
+  {
+    "Key": "decimal-type",
+    "Value": "Placeholder description for Decimal Type in Essential C#."
+  },
+  {
+    "Key": "literal-values",
+    "Value": "Placeholder description for Literal Values in Essential C#."
+  }
+]
diff --git a/EssentialCSharp.Web/Placeholders/sitemap.json b/EssentialCSharp.Web/Placeholders/sitemap.json
index c43e0b62..b4610023 100644
--- a/EssentialCSharp.Web/Placeholders/sitemap.json
+++ b/EssentialCSharp.Web/Placeholders/sitemap.json
@@ -3,6 +3,7 @@
     "Keys": [
       "introducing-c"
     ],
+    "PrimaryKey": "introducing-c",
     "PagePath": [
       "Chapters",
       "01",
@@ -17,12 +18,14 @@
     "ContentHash": "74B5",
     "AnchorId": "overview",
     "IndentLevel": 0,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "hello-world"
     ],
+    "PrimaryKey": "hello-world",
     "PagePath": [
       "Chapters",
       "01",
@@ -37,12 +40,14 @@
     "ContentHash": "C68C",
     "AnchorId": "hello-world",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "creating-editing-compiling-and-running-c-source-code"
     ],
+    "PrimaryKey": "creating-editing-compiling-and-running-c-source-code",
     "PagePath": [
       "Chapters",
       "01",
@@ -57,12 +62,14 @@
     "ContentHash": "8185",
     "AnchorId": "creating-editing-compiling-and-running-c-source-code",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "with-dotnet-cli"
     ],
+    "PrimaryKey": "with-dotnet-cli",
     "PagePath": [
       "Chapters",
       "01",
@@ -77,12 +84,14 @@
     "ContentHash": "E879",
     "AnchorId": "with-dotnet-cli",
     "IndentLevel": 3,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "with-visual-studio-2022-windows-or-mac"
     ],
+    "PrimaryKey": "with-visual-studio-2022-windows-or-mac",
     "PagePath": [
       "Chapters",
       "01",
@@ -97,12 +106,14 @@
     "ContentHash": "ECF8",
     "AnchorId": "with-visual-studio-2022-windows-or-mac",
     "IndentLevel": 3,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "understanding-a-project"
     ],
+    "PrimaryKey": "understanding-a-project",
     "PagePath": [
       "Chapters",
       "01",
@@ -117,12 +128,14 @@
     "ContentHash": "E9E5",
     "AnchorId": "understanding-a-project",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "compilation-and-execution"
     ],
+    "PrimaryKey": "compilation-and-execution",
     "PagePath": [
       "Chapters",
       "01",
@@ -137,12 +150,14 @@
     "ContentHash": "A4C6",
     "AnchorId": "compilation-and-execution",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "essential-c-source-code"
     ],
+    "PrimaryKey": "essential-c-source-code",
     "PagePath": [
       "Chapters",
       "01",
@@ -157,12 +172,14 @@
     "ContentHash": "527F",
     "AnchorId": "essential-c-source-code",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "c-syntax-fundamentals"
     ],
+    "PrimaryKey": "c-syntax-fundamentals",
     "PagePath": [
       "Chapters",
       "01",
@@ -177,12 +194,14 @@
     "ContentHash": "983A",
     "AnchorId": "c-syntax-fundamentals",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "statements-and-statement-delimiters"
     ],
+    "PrimaryKey": "statements-and-statement-delimiters",
     "PagePath": [
       "Chapters",
       "01",
@@ -197,12 +216,14 @@
     "ContentHash": "A624",
     "AnchorId": "statements-and-statement-delimiters",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "introducing-a-class-and-a-method"
     ],
+    "PrimaryKey": "introducing-a-class-and-a-method",
     "PagePath": [
       "Chapters",
       "01",
@@ -217,12 +238,14 @@
     "ContentHash": "F9FF",
     "AnchorId": "introducing-a-class-and-a-method",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "c-keywords"
     ],
+    "PrimaryKey": "c-keywords",
     "PagePath": [
       "Chapters",
       "01",
@@ -237,12 +260,14 @@
     "ContentHash": "1E24",
     "AnchorId": "c-keywords",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "identifiers"
     ],
+    "PrimaryKey": "identifiers",
     "PagePath": [
       "Chapters",
       "01",
@@ -257,12 +282,14 @@
     "ContentHash": "8156",
     "AnchorId": "identifiers",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "type-definition"
     ],
+    "PrimaryKey": "type-definition",
     "PagePath": [
       "Chapters",
       "01",
@@ -277,12 +304,14 @@
     "ContentHash": "FA33",
     "AnchorId": "type-definition",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "main-method"
     ],
+    "PrimaryKey": "main-method",
     "PagePath": [
       "Chapters",
       "01",
@@ -297,12 +326,14 @@
     "ContentHash": "52B1",
     "AnchorId": "main-method",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "whitespace"
     ],
+    "PrimaryKey": "whitespace",
     "PagePath": [
       "Chapters",
       "01",
@@ -317,12 +348,14 @@
     "ContentHash": "0151",
     "AnchorId": "whitespace",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "working-with-variables"
     ],
+    "PrimaryKey": "working-with-variables",
     "PagePath": [
       "Chapters",
       "01",
@@ -337,12 +370,14 @@
     "ContentHash": "134A",
     "AnchorId": "working-with-variables",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "introducing-data-types"
     ],
+    "PrimaryKey": "introducing-data-types",
     "PagePath": [
       "Chapters",
       "01",
@@ -357,12 +392,14 @@
     "ContentHash": "EC83",
     "AnchorId": "introducing-data-types",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "declaring-a-variable"
     ],
+    "PrimaryKey": "declaring-a-variable",
     "PagePath": [
       "Chapters",
       "01",
@@ -377,12 +414,14 @@
     "ContentHash": "98A8",
     "AnchorId": "declaring-a-variable",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "assigning-a-variable"
     ],
+    "PrimaryKey": "assigning-a-variable",
     "PagePath": [
       "Chapters",
       "01",
@@ -397,12 +436,14 @@
     "ContentHash": "0143",
     "AnchorId": "assigning-a-variable",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "using-a-variable"
     ],
+    "PrimaryKey": "using-a-variable",
     "PagePath": [
       "Chapters",
       "01",
@@ -417,12 +458,14 @@
     "ContentHash": "8C38",
     "AnchorId": "using-a-variable",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "console-input-and-output"
     ],
+    "PrimaryKey": "console-input-and-output",
     "PagePath": [
       "Chapters",
       "01",
@@ -437,12 +480,14 @@
     "ContentHash": "C93C",
     "AnchorId": "console-input-and-output",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "getting-input-from-the-console"
     ],
+    "PrimaryKey": "getting-input-from-the-console",
     "PagePath": [
       "Chapters",
       "01",
@@ -457,12 +502,14 @@
     "ContentHash": "A17C",
     "AnchorId": "getting-input-from-the-console",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "writing-output-to-the-console"
     ],
+    "PrimaryKey": "writing-output-to-the-console",
     "PagePath": [
       "Chapters",
       "01",
@@ -477,12 +524,14 @@
     "ContentHash": "A935",
     "AnchorId": "writing-output-to-the-console",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "comments"
     ],
+    "PrimaryKey": "comments",
     "PagePath": [
       "Chapters",
       "01",
@@ -497,12 +546,14 @@
     "ContentHash": "F51C",
     "AnchorId": "comments",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "debugging"
     ],
+    "PrimaryKey": "debugging",
     "PagePath": [
       "Chapters",
       "01",
@@ -517,12 +568,14 @@
     "ContentHash": "B9AA",
     "AnchorId": "debugging",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "managed-execution-and-the-common-language-infrastructure"
     ],
+    "PrimaryKey": "managed-execution-and-the-common-language-infrastructure",
     "PagePath": [
       "Chapters",
       "01",
@@ -537,12 +590,14 @@
     "ContentHash": "0B6A",
     "AnchorId": "managed-execution-and-the-common-language-infrastructure",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "common-intermediate-language-and-ildasm"
     ],
+    "PrimaryKey": "common-intermediate-language-and-ildasm",
     "PagePath": [
       "Chapters",
       "01",
@@ -557,12 +612,14 @@
     "ContentHash": "2200",
     "AnchorId": "common-intermediate-language-and-ildasm",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "multiple-net-frameworks"
     ],
+    "PrimaryKey": "multiple-net-frameworks",
     "PagePath": [
       "Chapters",
       "01",
@@ -577,12 +634,14 @@
     "ContentHash": "9CE9",
     "AnchorId": "multiple-net-frameworks",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "application-programming-interface"
     ],
+    "PrimaryKey": "application-programming-interface",
     "PagePath": [
       "Chapters",
       "01",
@@ -597,12 +656,14 @@
     "ContentHash": "941F",
     "AnchorId": "application-programming-interface",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "c-and-net-versioning"
     ],
+    "PrimaryKey": "c-and-net-versioning",
     "PagePath": [
       "Chapters",
       "01",
@@ -617,12 +678,14 @@
     "ContentHash": "3503",
     "AnchorId": "c-and-net-versioning",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "chapter-1-summary"
     ],
+    "PrimaryKey": "chapter-1-summary",
     "PagePath": [
       "Chapters",
       "01",
@@ -637,12 +700,14 @@
     "ContentHash": "DE96",
     "AnchorId": "chapter-1-summary",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "data-types"
     ],
+    "PrimaryKey": "data-types",
     "PagePath": [
       "Chapters",
       "02",
@@ -657,12 +722,14 @@
     "ContentHash": "61DD",
     "AnchorId": "overview",
     "IndentLevel": 0,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "type-name-forms"
     ],
+    "PrimaryKey": "type-name-forms",
     "PagePath": [
       "Chapters",
       "02",
@@ -677,12 +744,14 @@
     "ContentHash": "BAB3",
     "AnchorId": "type-name-forms",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "fundamental-numeric-types"
     ],
+    "PrimaryKey": "fundamental-numeric-types",
     "PagePath": [
       "Chapters",
       "02",
@@ -697,12 +766,14 @@
     "ContentHash": "7EC2",
     "AnchorId": "fundamental-numeric-types",
     "IndentLevel": 1,
-    "IncludeInSitemapXml": true
+    "IncludeInSitemapXml": true,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "integer-types"
     ],
+    "PrimaryKey": "integer-types",
     "PagePath": [
       "Chapters",
       "02",
@@ -717,12 +788,14 @@
     "ContentHash": "FB7E",
     "AnchorId": "integer-types",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "floating-point-types-float-double"
     ],
+    "PrimaryKey": "floating-point-types-float-double",
     "PagePath": [
       "Chapters",
       "02",
@@ -737,12 +810,14 @@
     "ContentHash": "95AB",
     "AnchorId": "floating-point-types-float-double",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "decimal-type"
     ],
+    "PrimaryKey": "decimal-type",
     "PagePath": [
       "Chapters",
       "02",
@@ -757,12 +832,14 @@
     "ContentHash": "7C20",
     "AnchorId": "decimal-type",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   },
   {
     "Keys": [
       "literal-values"
     ],
+    "PrimaryKey": "literal-values",
     "PagePath": [
       "Chapters",
       "02",
@@ -777,6 +854,7 @@
     "ContentHash": "BFB8",
     "AnchorId": "literal-values",
     "IndentLevel": 2,
-    "IncludeInSitemapXml": false
+    "IncludeInSitemapXml": false,
+    "LastModified": "2025-07-11T20:01:19.0699112Z"
   }
 ]
\ No newline at end of file
diff --git a/EssentialCSharp.Web/Program.cs b/EssentialCSharp.Web/Program.cs
index 1cb4de2a..95a8cbbe 100644
--- a/EssentialCSharp.Web/Program.cs
+++ b/EssentialCSharp.Web/Program.cs
@@ -615,6 +615,11 @@ await McpJsonRpcResponseWriter.WriteErrorAsync(
 
         app.MapFallbackToController("Index", "Home");
 
+        // Construct content-backed singletons now so an unreadable content file fails startup (the new
+        // revision never takes traffic) instead of surfacing as a 500 on the first page request.
+        app.Services.GetRequiredService<ChapterDescriptionService>();
+        app.Services.GetRequiredService<IGuidelinesService>();
+
         // Validate sitemap data at startup — logs errors but allows startup to continue
         var siteMappingService = app.Services.GetRequiredService<ISiteMappingService>();
         var logger = app.Services.GetRequiredService<ILogger<Program>>();
diff --git a/EssentialCSharp.Web/Services/ChapterDescriptionService.cs b/EssentialCSharp.Web/Services/ChapterDescriptionService.cs
index f4cc60bb..f2a24434 100644
--- a/EssentialCSharp.Web/Services/ChapterDescriptionService.cs
+++ b/EssentialCSharp.Web/Services/ChapterDescriptionService.cs
@@ -6,6 +6,9 @@ public sealed class ChapterDescriptionService
 {
     private readonly Dictionary<string, string> _Descriptions;
 
+    /// <summary>Number of descriptions loaded from sitemap.descriptions.json (0 when the file is absent).</summary>
+    public int Count => _Descriptions.Count;
+
     public ChapterDescriptionService(IWebHostEnvironment environment)
     {
         string path = Path.Combine(environment.ContentRootPath, "Chapters", "sitemap.descriptions.json");
@@ -16,19 +19,71 @@ public ChapterDescriptionService(IWebHostEnvironment environment)
         }
 
         using FileStream stream = File.OpenRead(path);
-        List<SiteMappingDescription> entries = JsonSerializer.Deserialize<List<SiteMappingDescription>>(stream)
-            ?? throw new InvalidDataException($"No chapter descriptions found in {path}");
+        using JsonDocument document = JsonDocument.Parse(stream);
+        if (document.RootElement.ValueKind != JsonValueKind.Array)
+        {
+            throw new InvalidDataException($"Expected a JSON array of chapter descriptions in {path}");
+        }
+
         Dictionary<string, string> descriptions = new(StringComparer.OrdinalIgnoreCase);
-        foreach (SiteMappingDescription entry in entries)
+        int index = 0;
+        foreach (JsonElement entry in document.RootElement.EnumerateArray())
         {
-            foreach (string key in entry.Keys)
+            string value = ReadValue(entry, path, index);
+            foreach (string key in ReadKeys(entry, path, index))
             {
-                descriptions.Add(key, entry.Value);
+                descriptions.Add(key, value);
             }
+            index++;
         }
         _Descriptions = descriptions;
     }
 
+    // The content package has emitted { "Key": "..." } while the shared SiteMappingDescription type
+    // declares "Keys". Accept both so a mismatch between the two cannot take the site down.
+    private static List<string> ReadKeys(JsonElement entry, string path, int index)
+    {
+        if (entry.ValueKind == JsonValueKind.Object)
+        {
+            if (entry.TryGetProperty("Keys", out JsonElement keys) && keys.ValueKind == JsonValueKind.Array)
+            {
+                List<string> result = [];
+                foreach (JsonElement key in keys.EnumerateArray())
+                {
+                    string? text = key.ValueKind == JsonValueKind.String ? key.GetString() : null;
+                    result.Add(!string.IsNullOrWhiteSpace(text) ? text : throw InvalidEntry(path, index, "contains an empty key"));
+                }
+                return result;
+            }
+
+            if (entry.TryGetProperty("Key", out JsonElement singleKey) && singleKey.ValueKind == JsonValueKind.String)
+            {
+                string? text = singleKey.GetString();
+                if (!string.IsNullOrWhiteSpace(text))
+                {
+                    return [text];
+                }
+            }
+        }
+
+        throw InvalidEntry(path, index, "has neither a \"Keys\" array nor a \"Key\" string");
+    }
+
+    private static string ReadValue(JsonElement entry, string path, int index)
+    {
+        if (entry.ValueKind == JsonValueKind.Object
+            && entry.TryGetProperty("Value", out JsonElement value) && value.ValueKind == JsonValueKind.String
+            && value.GetString() is string text)
+        {
+            return text;
+        }
+
+        throw InvalidEntry(path, index, "has no \"Value\" string");
+    }
+
+    private static InvalidDataException InvalidEntry(string path, int index, string problem) =>
+        new($"Chapter description entry {index} in {path} {problem}");
+
     public string GetDescription(SiteMapping mapping)
     {
         foreach (string key in mapping.Keys)
diff --git a/scripts/smoke-test.sh b/scripts/smoke-test.sh
new file mode 100755
index 00000000..fe75d4d9
--- /dev/null
+++ b/scripts/smoke-test.sh
@@ -0,0 +1,15 @@
+#!/usr/bin/env bash
+# Requests the health endpoint plus real pages. Usage: smoke-test.sh <fqdn>
+set -euo pipefail
+
+fqdn="${1:?usage: smoke-test.sh <fqdn>}"
+
+# /health stays green when content-backed services are broken, so also request pages that need them.
+paths=(/health / /hello-world /guidelines)
+
+for path in "${paths[@]}"; do
+  echo "GET https://${fqdn}${path}"
+  # --retry-all-errors ensures HTTP 5xx (cold-start 503s) also trigger retries; -L follows page redirects
+  curl --fail --silent --show-error --location --retry 10 --retry-delay 15 --retry-all-errors --max-time 30 \
+    --output /dev/null --write-out '  -> %{http_code}\n' "https://${fqdn}${path}"
+done