(bugfix): ACME rate limits, cooldown persistence, and LetsEncrypt hardening

CHANGELOG.md

@@ -4,6 +4,28 @@ All notable changes to this project will be documented in this file.
 
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.1.0/), and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
+## [3.3.6] - 2026-04-13
+
+### Added
+
+- **LetsEncrypt:** Per-host ACME rate-limit cooldown on `RegistrationCache` (`AcmeRenewalNotBeforeUtcByHostname`), with HTTP `Retry-After` and problem-detail parsing (`AcmeRetryAfterParser`), structured logging, and `Result.TooManyRequests` when the CA returns `rateLimited`.
+- **LetsEncrypt:** `AcmeProblemKind` as an `Enumeration` (RFC 8555 problem `type` URIs) instead of ad hoc strings; `LetsEncrytException` exposes `ProblemKind`, `RetryAfterUtc`, and optional rate-limit hostname.
+- **LetsEncrypt:** `AcmeSessionStore` for per-session `State` in memory; `LetsEncryptService` split into partial files (`LetsEncryptService.Helpers.cs`) for HTTP/JWS/error helpers.
+- **LetsEncrypt:** `State.TryGetAccountKey` for a single place to validate account key material after `Init`.
+- **LetsEncrypt.Tests:** Unit tests for retry parsing, problem-kind resolution, and cooldown JSON round-trip.
+
+### Changed
+
+- **AutoRenewal:** Skips hostnames that are still in an ACME cooldown window (with debug logs for skipped hosts).
+- **Certs flow:** Persists registration cache after failed full certificate flows when a session exists so cooldown metadata is saved.
+- **LetsEncrypt:** Broader nullable reference annotations on ACME DTOs (`Problem`, `AcmeDirectory`, `AuthorizationChallengeError`, etc.) and explicit null guards in `LetsEncryptService`.
+
+### Fixed
+
+- **LetsEncrypt:** Certificate PEM loading uses `X509Certificate2.CreateFromPem` instead of the obsolete `X509Certificate2(byte[])` constructor (SYSLIB0057).
+- **LetsEncrypt:** `RevokeCertificate` now fails correctly on non-success responses (missing `return`), uses the same problem-document handling as other ACME calls, and disposes the HTTP response on successful revoke.
+- **LetsEncrypt:** `NewOrder` authorization error log line now logs the authorization status, not the order status.
+
 ## [3.3.5] - 2026-04-12
 
 ### Changed

assets/badges/coverage-lines.svg

@@ -1,5 +1,5 @@
-<svg xmlns="http://www.w3.org/2000/svg" width="137" height="20" role="img" aria-label="Line Coverage: 21.7%">
+<svg xmlns="http://www.w3.org/2000/svg" width="137" height="20" role="img" aria-label="Line Coverage: 21.6%">
-  <title>Line Coverage: 21.7%</title>
+  <title>Line Coverage: 21.6%</title>
   <linearGradient id="s" x2="0" y2="100%">
     <stop offset="0" stop-color="#bbb" stop-opacity=".1"/>
     <stop offset="1" stop-opacity=".1"/>
@@ -15,7 +15,7 @@
   <g fill="#fff" text-anchor="middle" font-family="Verdana,Geneva,DejaVu Sans,sans-serif" text-rendering="geometricPrecision" font-size="11">
     <text aria-hidden="true" x="47.25" y="15" fill="#010101" fill-opacity=".3">Line Coverage</text>
     <text x="47.25" y="14" fill="#fff">Line Coverage</text>
-    <text aria-hidden="true" x="115.75" y="15" fill="#010101" fill-opacity=".3">21.7%</text>
+    <text aria-hidden="true" x="115.75" y="15" fill="#010101" fill-opacity=".3">21.6%</text>
-    <text x="115.75" y="14" fill="#fff">21.7%</text>
+    <text x="115.75" y="14" fill="#fff">21.6%</text>
   </g>
 </svg>

assets/badges/coverage-methods.svg

@@ -1,5 +1,5 @@
-<svg xmlns="http://www.w3.org/2000/svg" width="150" height="20" role="img" aria-label="Method Coverage: 29.7%">
+<svg xmlns="http://www.w3.org/2000/svg" width="150" height="20" role="img" aria-label="Method Coverage: 31.5%">
-  <title>Method Coverage: 29.7%</title>
+  <title>Method Coverage: 31.5%</title>
   <linearGradient id="s" x2="0" y2="100%">
     <stop offset="0" stop-color="#bbb" stop-opacity=".1"/>
     <stop offset="1" stop-opacity=".1"/>
@@ -15,7 +15,7 @@
   <g fill="#fff" text-anchor="middle" font-family="Verdana,Geneva,DejaVu Sans,sans-serif" text-rendering="geometricPrecision" font-size="11">
     <text aria-hidden="true" x="53.75" y="15" fill="#010101" fill-opacity=".3">Method Coverage</text>
     <text x="53.75" y="14" fill="#fff">Method Coverage</text>
-    <text aria-hidden="true" x="128.75" y="15" fill="#010101" fill-opacity=".3">29.7%</text>
+    <text aria-hidden="true" x="128.75" y="15" fill="#010101" fill-opacity=".3">31.5%</text>
-    <text x="128.75" y="14" fill="#fff">29.7%</text>
+    <text x="128.75" y="14" fill="#fff">31.5%</text>
   </g>
 </svg>

src/LetsEncrypt.Tests/AcmeProblemKindTests.cs

@@ -0,0 +1,28 @@
+using MaksIT.LetsEncrypt;
+using Xunit;
+
+namespace MaksIT.LetsEncrypt.Tests;
+
+public class AcmeProblemKindTests {
+  [Theory]
+  [InlineData("urn:ietf:params:acme:error:rateLimited")]
+  [InlineData("urn:ietf:params:acme:error:badNonce")]
+  [InlineData("urn:ietf:params:acme:error:malformed")]
+  [InlineData("urn:ietf:params:acme:error:serverInternal")]
+  public void FromTypeUri_maps_rfc8555_uris(string uri) {
+    var kind = AcmeProblemKind.FromTypeUri(uri);
+    Assert.Equal(uri, kind.Name);
+  }
+
+  [Fact]
+  public void FromTypeUri_unknown_or_empty_returns_unknown() {
+    Assert.Same(AcmeProblemKind.Unknown, AcmeProblemKind.FromTypeUri(null));
+    Assert.Same(AcmeProblemKind.Unknown, AcmeProblemKind.FromTypeUri(""));
+    Assert.Same(AcmeProblemKind.Unknown, AcmeProblemKind.FromTypeUri("urn:ietf:params:acme:error:customVendorThing"));
+  }
+
+  [Fact]
+  public void FromTypeUri_is_case_sensitive_for_full_uri() {
+    Assert.Same(AcmeProblemKind.Unknown, AcmeProblemKind.FromTypeUri("urn:ietf:params:acme:error:RATELIMITED"));
+  }
+}

src/LetsEncrypt.Tests/AcmeRetryAfterParserTests.cs

@@ -0,0 +1,72 @@
+using System.Net.Http.Headers;
+using MaksIT.LetsEncrypt.Models.Responses;
+using Xunit;
+
+namespace MaksIT.LetsEncrypt.Tests;
+
+public class AcmeRetryAfterParserTests {
+  [Fact]
+  public void TryParseRetryAfterHttpHeader_reads_delta_seconds() {
+    using var response = new HttpResponseMessage();
+    response.Headers.RetryAfter = new RetryConditionHeaderValue(TimeSpan.FromSeconds(90));
+
+    var parsed = AcmeRetryAfterParser.TryParseRetryAfterHttpHeader(response);
+
+    Assert.NotNull(parsed);
+    var skew = (parsed.Value - DateTimeOffset.UtcNow.AddSeconds(90)).TotalSeconds;
+    Assert.InRange(skew, -2, 2);
+  }
+
+  [Fact]
+  public void TryParseRetryAfterHttpHeader_reads_absolute_date() {
+    using var response = new HttpResponseMessage();
+    var when = new DateTimeOffset(2026, 4, 12, 17, 49, 19, TimeSpan.Zero);
+    response.Headers.RetryAfter = new RetryConditionHeaderValue(when);
+
+    var parsed = AcmeRetryAfterParser.TryParseRetryAfterHttpHeader(response);
+
+    Assert.Equal(when, parsed);
+  }
+
+  [Fact]
+  public void TryParseRetryAfterFromDetail_parses_lets_encrypt_sample() {
+    const string detail =
+      "urn:ietf:params:acme:error:rateLimited: too many failed authorizations (5) for \"cloud.maks-it.com\" in the last 1h0m0s, retry after 2026-04-12 17:49:19 UTC: see https://letsencrypt.org/docs/rate-limits/";
+
+    var parsed = AcmeRetryAfterParser.TryParseRetryAfterFromDetail(detail);
+
+    Assert.NotNull(parsed);
+    Assert.Equal(2026, parsed.Value.Year);
+    Assert.Equal(4, parsed.Value.Month);
+    Assert.Equal(12, parsed.Value.Day);
+    Assert.Equal(17, parsed.Value.Hour);
+    Assert.Equal(49, parsed.Value.Minute);
+  }
+
+  [Fact]
+  public void TryParseRateLimitedHostname_extracts_identifier() {
+    const string detail =
+      "too many failed authorizations (5) for \"cloud.maks-it.com\" in the last 1h0m0s, retry after 2026-04-12 17:49:19 UTC";
+
+    var host = AcmeRetryAfterParser.TryParseRateLimitedHostname(detail);
+
+    Assert.Equal("cloud.maks-it.com", host);
+  }
+
+  [Fact]
+  public void TryCombineRetryAfterUtc_takes_later_of_header_and_detail() {
+    using var response = new HttpResponseMessage();
+    response.Headers.RetryAfter = new RetryConditionHeaderValue(new DateTimeOffset(2026, 4, 12, 12, 0, 0, TimeSpan.Zero));
+
+    var problem = new Problem {
+      Type = "urn:ietf:params:acme:error:rateLimited",
+      Detail = "retry after 2026-04-12 18:00:00 UTC",
+      RawJson = ""
+    };
+
+    var combined = AcmeRetryAfterParser.TryCombineRetryAfterUtc(response, problem);
+
+    Assert.NotNull(combined);
+    Assert.Equal(18, combined.Value.Hour);
+  }
+}

src/LetsEncrypt.Tests/RegistrationCacheAcmeCooldownSerializationTests.cs

@@ -0,0 +1,30 @@
+using MaksIT.Core.Extensions;
+using MaksIT.LetsEncrypt.Entities;
+using Xunit;
+
+namespace MaksIT.LetsEncrypt.Tests;
+
+public class RegistrationCacheAcmeCooldownSerializationTests {
+  [Fact]
+  public void AcmeRenewalNotBeforeUtcByHostname_round_trips_json() {
+    var until = new DateTimeOffset(2026, 4, 12, 17, 49, 19, TimeSpan.Zero);
+    var cache = new RegistrationCache {
+      AccountId = Guid.Parse("aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee"),
+      Description = "test",
+      Contacts = ["ops@example.com"],
+      IsStaging = true,
+      ChallengeType = "http-01",
+      AcmeRenewalNotBeforeUtcByHostname = new Dictionary<string, DateTimeOffset>(StringComparer.OrdinalIgnoreCase) {
+        ["cloud.example.com"] = until
+      }
+    };
+
+    var json = cache.ToJson();
+    var restored = json.ToObject<RegistrationCache>();
+
+    Assert.NotNull(restored);
+    Assert.NotNull(restored!.AcmeRenewalNotBeforeUtcByHostname);
+    Assert.True(restored.AcmeRenewalNotBeforeUtcByHostname!.TryGetValue("cloud.example.com", out var v));
+    Assert.Equal(until, v);
+  }
+}

src/LetsEncrypt/AcmeProblemKind.cs

@@ -0,0 +1,52 @@
+using MaksIT.Core.Abstractions;
+
+namespace MaksIT.LetsEncrypt;
+
+/// <summary>
+/// ACME problem <c>type</c> URIs (RFC 8555 §6.7). <see cref="Unknown"/> covers missing or unrecognized URIs.
+/// </summary>
+public sealed class AcmeProblemKind : Enumeration {
+
+  public static readonly AcmeProblemKind Unknown = new(0, "");
+
+  public static readonly AcmeProblemKind BadCsr = new(1, "urn:ietf:params:acme:error:badCSR");
+  public static readonly AcmeProblemKind BadNonce = new(2, "urn:ietf:params:acme:error:badNonce");
+  public static readonly AcmeProblemKind BadPublicKey = new(3, "urn:ietf:params:acme:error:badPublicKey");
+  public static readonly AcmeProblemKind BadRevocationReason = new(4, "urn:ietf:params:acme:error:badRevocationReason");
+  public static readonly AcmeProblemKind BadSignatureAlgorithm = new(5, "urn:ietf:params:acme:error:badSignatureAlgorithm");
+  public static readonly AcmeProblemKind Caa = new(6, "urn:ietf:params:acme:error:caa");
+  public static readonly AcmeProblemKind Compound = new(7, "urn:ietf:params:acme:error:compound");
+  public static readonly AcmeProblemKind Connection = new(8, "urn:ietf:params:acme:error:connection");
+  public static readonly AcmeProblemKind Dns = new(9, "urn:ietf:params:acme:error:dns");
+  public static readonly AcmeProblemKind ExternalAccountRequired = new(10, "urn:ietf:params:acme:error:externalAccountRequired");
+  public static readonly AcmeProblemKind IncorrectResponse = new(11, "urn:ietf:params:acme:error:incorrectResponse");
+  public static readonly AcmeProblemKind InvalidContact = new(12, "urn:ietf:params:acme:error:invalidContact");
+  public static readonly AcmeProblemKind Malformed = new(13, "urn:ietf:params:acme:error:malformed");
+  public static readonly AcmeProblemKind OrderNotReady = new(14, "urn:ietf:params:acme:error:orderNotReady");
+  public static readonly AcmeProblemKind RateLimited = new(15, "urn:ietf:params:acme:error:rateLimited");
+  public static readonly AcmeProblemKind RejectedIdentifier = new(16, "urn:ietf:params:acme:error:rejectedIdentifier");
+  public static readonly AcmeProblemKind ServerInternal = new(17, "urn:ietf:params:acme:error:serverInternal");
+  public static readonly AcmeProblemKind Tls = new(18, "urn:ietf:params:acme:error:tls");
+  public static readonly AcmeProblemKind UnsupportedContact = new(19, "urn:ietf:params:acme:error:unsupportedContact");
+  public static readonly AcmeProblemKind UnsupportedIdentifier = new(20, "urn:ietf:params:acme:error:unsupportedIdentifier");
+  public static readonly AcmeProblemKind UserActionRequired = new(21, "urn:ietf:params:acme:error:userActionRequired");
+
+  private AcmeProblemKind(int id, string name) : base(id, name) { }
+
+  /// <summary>
+  /// Resolves a problem <c>type</c> URI from the CA. Comparison is ordinal (RFC 3986).
+  /// </summary>
+  public static AcmeProblemKind FromTypeUri(string? typeUri) {
+    if (string.IsNullOrEmpty(typeUri))
+      return Unknown;
+
+    foreach (var kind in GetAll<AcmeProblemKind>()) {
+      if (kind == Unknown)
+        continue;
+      if (kind.Name == typeUri)
+        return kind;
+    }
+
+    return Unknown;
+  }
+}

src/LetsEncrypt/AcmeRetryAfterParser.cs

@@ -0,0 +1,66 @@
+using System.Globalization;
+using System.Net.Http;
+using System.Text.RegularExpressions;
+using MaksIT.LetsEncrypt.Models.Responses;
+
+namespace MaksIT.LetsEncrypt;
+
+internal static class AcmeRetryAfterParser {
+  private static readonly Regex RetryAfterDetailRegex = new(
+    @"retry\s+after\s+(?<ts>\d{4}-\d{2}-\d{2}\s+\d{2}:\d{2}:\d{2})\s+UTC",
+    RegexOptions.IgnoreCase | RegexOptions.CultureInvariant);
+
+  private static readonly Regex RateLimitedHostRegex = new(
+    @"for\s+""(?<host>[^""]+)""",
+    RegexOptions.IgnoreCase | RegexOptions.CultureInvariant);
+
+  internal static DateTimeOffset? TryParseRetryAfterHttpHeader(HttpResponseMessage? response) {
+    if (response?.Headers.RetryAfter is not { } ra)
+      return null;
+
+    if (ra.Date is { } absolute)
+      return new DateTimeOffset(absolute.UtcDateTime, TimeSpan.Zero);
+
+    if (ra.Delta is { } delta)
+      return DateTimeOffset.UtcNow + delta;
+
+    return null;
+  }
+
+  internal static DateTimeOffset? TryParseRetryAfterFromDetail(string? detail) {
+    if (string.IsNullOrEmpty(detail))
+      return null;
+
+    var m = RetryAfterDetailRegex.Match(detail);
+    if (!m.Success)
+      return null;
+
+    var ts = m.Groups["ts"].Value;
+    if (DateTimeOffset.TryParseExact(ts, "yyyy-MM-dd HH:mm:ss", CultureInfo.InvariantCulture,
+          DateTimeStyles.AssumeUniversal | DateTimeStyles.AdjustToUniversal, out var dto))
+      return dto;
+
+    return null;
+  }
+
+  /// <summary>
+  /// Latest of header and detail-derived times (stricter / later wins). Null if neither present.
+  /// </summary>
+  internal static DateTimeOffset? TryCombineRetryAfterUtc(HttpResponseMessage? response, Problem? problem) {
+    var fromHeader = TryParseRetryAfterHttpHeader(response);
+    var fromDetail = TryParseRetryAfterFromDetail(problem?.Detail);
+
+    if (fromHeader.HasValue && fromDetail.HasValue)
+      return fromHeader.Value > fromDetail.Value ? fromHeader.Value : fromDetail.Value;
+
+    return fromHeader ?? fromDetail;
+  }
+
+  internal static string? TryParseRateLimitedHostname(string? detail) {
+    if (string.IsNullOrEmpty(detail))
+      return null;
+
+    var m = RateLimitedHostRegex.Match(detail);
+    return m.Success ? m.Groups["host"].Value : null;
+  }
+}

src/LetsEncrypt/Entities/LetsEncrypt/RegistrationCache.cs

@@ -23,6 +23,13 @@ public class RegistrationCache {
 
 
   public Dictionary<string, CertificateCache>? CachedCerts { get; set; }
+
+  /// <summary>
+  /// Earliest UTC instant when renewal may be attempted again for each hostname (e.g. after ACME rate limit).
+  /// Keys use the same DNS names as <see cref="CachedCerts"/>.
+  /// </summary>
+  public Dictionary<string, DateTimeOffset>? AcmeRenewalNotBeforeUtcByHostname { get; set; }
+
   public byte[]? AccountKey { get; set; }
   public string? Id { get; set; }
   public Jwk? Key { get; set; }
@@ -77,6 +84,36 @@ public class RegistrationCache {
     return hosts.ToArray();
   }
 
+  /// <summary>
+  /// True if the hostname must not be renewed yet due to a stored ACME cooldown.
+  /// </summary>
+  public bool IsHostnameInAcmeCooldown(string hostname, out DateTimeOffset notBeforeUtc) {
+    notBeforeUtc = default;
+    if (AcmeRenewalNotBeforeUtcByHostname == null)
+      return false;
+
+    foreach (var kvp in AcmeRenewalNotBeforeUtcByHostname) {
+      if (!string.Equals(kvp.Key, hostname, StringComparison.OrdinalIgnoreCase))
+        continue;
+      if (kvp.Value <= DateTimeOffset.UtcNow)
+        return false;
+      notBeforeUtc = kvp.Value;
+      return true;
+    }
+
+    return false;
+  }
+
+  public void ClearAcmeCooldownForHostname(string hostname) {
+    if (AcmeRenewalNotBeforeUtcByHostname == null)
+      return;
+
+    var key = AcmeRenewalNotBeforeUtcByHostname.Keys
+      .FirstOrDefault(k => string.Equals(k, hostname, StringComparison.OrdinalIgnoreCase));
+    if (key != null)
+      AcmeRenewalNotBeforeUtcByHostname.Remove(key);
+  }
+
   /// <summary>
   /// Returns cached certificate. Certs older than 30 days are not returned
   /// </summary>

src/LetsEncrypt/Entities/LetsEncrypt/State.cs

@@ -1,7 +1,7 @@
-using MaksIT.Core.Security.JWK;
+using System.Diagnostics.CodeAnalysis;
-using MaksIT.LetsEncrypt.Models.Responses;
 using System.Security.Cryptography;
-
+using MaksIT.Core.Security.JWK;
+using MaksIT.LetsEncrypt.Models.Responses;
 
 namespace MaksIT.LetsEncrypt.Entities.LetsEncrypt;
 
@@ -13,4 +13,11 @@ public class State {
   public RegistrationCache? Cache { get; set; }
   public Jwk? Jwk { get; set; }
   public RSA? Rsa { get; set; }
+
+  /// <summary>Returns the session account key pair when both RSA and JWK are present (after <c>Init</c>).</summary>
+  public bool TryGetAccountKey([NotNullWhen(true)] out RSA? rsa, [NotNullWhen(true)] out Jwk? jwk) {
+    rsa = Rsa;
+    jwk = Jwk;
+    return rsa is not null && jwk is not null;
+  }
 }

src/LetsEncrypt/Exceptions/LetsEncrytException.cs

@@ -1,20 +1,44 @@
-using MaksIT.LetsEncrypt.Models.Responses;
+using MaksIT.LetsEncrypt;
-
+using MaksIT.LetsEncrypt.Models.Responses;
 
 namespace MaksIT.LetsEncrypt.Exceptions;
 
+/// <summary>Thrown when the ACME server returns a problem document or challenge error.</summary>
+/// <remarks>
+/// <see cref="Response"/> implements <see cref="IDisposable"/>. <see cref="Services.LetsEncryptService"/> disposes it
+/// when mapping this exception to a <see cref="MaksIT.Core.Results.Result"/>; any other handler must dispose it to avoid holding connections.
+/// </remarks>
 public class LetsEncrytException : Exception {
 
   public Problem? Problem { get; }
 
+  /// <summary>HTTP response that carried the problem (must be disposed if this exception is not handled by <see cref="Services.LetsEncryptService"/>).</summary>
   public HttpResponseMessage Response { get; }
 
+  /// <summary>Classified <c>type</c> from the ACME problem document (RFC 8555 §6.7).</summary>
+  public AcmeProblemKind ProblemKind { get; }
+
+  /// <summary>Combined Retry-After from HTTP header and problem detail, when present.</summary>
+  public DateTimeOffset? RetryAfterUtc { get; }
+
+  /// <summary>Hostname from Let's Encrypt rate-limit <c>detail</c>, when parseable.</summary>
+  public string? RateLimitedIdentifier { get; }
+
+  public bool IsRateLimited => ProblemKind == AcmeProblemKind.RateLimited;
+
   public LetsEncrytException(
     Problem? problem,
     HttpResponseMessage response
-  ) : base(problem != null ? $"{problem.Type}: {problem.Detail}" : "") {
+  ) : base(problem != null
+      ? $"{problem.Type}: {problem.Detail}"
+      : $"HTTP {(int)(response ?? throw new ArgumentNullException(nameof(response))).StatusCode}") {
 
+    ArgumentNullException.ThrowIfNull(response);
     Problem = problem;
     Response = response;
+    ProblemKind = AcmeProblemKind.FromTypeUri(problem?.Type);
+    RetryAfterUtc = AcmeRetryAfterParser.TryCombineRetryAfterUtc(response, problem);
+    if (ProblemKind == AcmeProblemKind.RateLimited)
+      RateLimitedIdentifier = AcmeRetryAfterParser.TryParseRateLimitedHostname(problem?.Detail);
   }
 }

src/LetsEncrypt/Extensions/ServiceCollectionExtensions.cs

@@ -14,6 +14,7 @@ public static class ServiceCollectionExtensions {
     };
 
     services.AddSingleton(config);
+    services.AddSingleton<AcmeSessionStore>();
     services.AddHttpClient<ILetsEncryptService, LetsEncryptService>();
   }
 }

src/LetsEncrypt/LetsEncrypt.csproj

@@ -7,6 +7,10 @@
     <RootNamespace>MaksIT.$(MSBuildProjectName.Replace(" ", "_"))</RootNamespace>
   </PropertyGroup>
 
+  <ItemGroup>
+    <InternalsVisibleTo Include="LetsEncrypt.Tests" />
+  </ItemGroup>
+
   <ItemGroup>
     <PackageReference Include="MaksIT.Core" Version="1.6.5" />
     <PackageReference Include="MaksIT.Results" Version="2.0.1" />

src/LetsEncrypt/Models/Responses/AcmeDirectory.cs

@@ -1,17 +1,17 @@
 namespace MaksIT.LetsEncrypt.Models.Responses;
 
 public class AcmeDirectory {
-  public Uri KeyChange { get; set; }
+  public Uri? KeyChange { get; set; }
-  public AcmeDirectoryMeta Meta { get; set; }
+  public AcmeDirectoryMeta? Meta { get; set; }
-  public Uri NewAccount { get; set; }
+  public Uri? NewAccount { get; set; }
-  public Uri NewNonce { get; set; }
+  public Uri? NewNonce { get; set; }
-  public Uri NewOrder { get; set; }
+  public Uri? NewOrder { get; set; }
-  public Uri RenewalInfo { get; set; }
+  public Uri? RenewalInfo { get; set; }
-  public Uri RevokeCert { get; set; }  
+  public Uri? RevokeCert { get; set; }
 }
 
 public class AcmeDirectoryMeta {
-  public string[] CaaIdentities { get; set; }
+  public string[]? CaaIdentities { get; set; }
-  public string TermsOfService { get; set; }
+  public string? TermsOfService { get; set; }
-  public string Website { get; set; }
+  public string? Website { get; set; }
 }

src/LetsEncrypt/Models/Responses/AuthorizationChallengeError.cs

@@ -6,7 +6,7 @@ using System.Threading.Tasks;
 
 namespace MaksIT.LetsEncrypt.Models.Responses;
 public class AuthorizationChallengeError {
-  public string Type { get; set; }
+  public string? Type { get; set; }
 
-  public string Detail { get; set; }
+  public string? Detail { get; set; }
 }

src/LetsEncrypt/Models/Responses/Problem.cs

@@ -6,10 +6,10 @@ using System.Threading.Tasks;
 
 namespace MaksIT.LetsEncrypt.Models.Responses {
   public class Problem {
-    public string Type { get; set; }
+    public string? Type { get; set; }
 
-    public string Detail { get; set; }
+    public string? Detail { get; set; }
 
-    public string RawJson { get; set; }
+    public string? RawJson { get; set; }
   }
 }

src/LetsEncrypt/Services/AcmeSessionStore.cs

@@ -0,0 +1,21 @@
+using MaksIT.LetsEncrypt.Entities.LetsEncrypt;
+using Microsoft.Extensions.Caching.Memory;
+
+namespace MaksIT.LetsEncrypt.Services;
+
+/// <summary>Caches per-session <see cref="State"/> for ACME flows (directory, account, current order, challenges).</summary>
+public sealed class AcmeSessionStore {
+  private static readonly TimeSpan SessionTtl = TimeSpan.FromHours(1);
+
+  private readonly IMemoryCache _cache;
+
+  public AcmeSessionStore(IMemoryCache cache) => _cache = cache;
+
+  public State GetOrCreate(Guid sessionId) {
+    if (!_cache.TryGetValue(sessionId, out State? state) || state is null) {
+      state = new State();
+      _cache.Set(sessionId, state, SessionTtl);
+    }
+    return state;
+  }
+}

src/LetsEncrypt/Services/LetsEncryptService.Helpers.cs

@@ -0,0 +1,235 @@
+using System.Net.Http.Headers;
+using Microsoft.Extensions.Logging;
+using MaksIT.Core.Extensions;
+using MaksIT.Core.Security.JWS;
+using MaksIT.LetsEncrypt.Entities;
+using MaksIT.LetsEncrypt.Entities.Jws;
+using MaksIT.LetsEncrypt.Entities.LetsEncrypt;
+using MaksIT.LetsEncrypt.Exceptions;
+using MaksIT.LetsEncrypt.Models.Interfaces;
+using MaksIT.LetsEncrypt.Models.Responses;
+using MaksIT.Results;
+
+
+namespace MaksIT.LetsEncrypt.Services;
+
+public partial class LetsEncryptService {
+
+  #region Internal helpers
+
+  private State GetOrCreateState(Guid sessionId) => _sessions.GetOrCreate(sessionId);
+
+  private async Task<Result<string?>> GetNonceAsync(Guid sessionId, Uri uri) {
+    if (uri == null)
+      return Result<string?>.InternalServerError(null, "URI is null");
+
+    try {
+      var state = GetOrCreateState(sessionId);
+
+      _logger.LogInformation($"Executing {nameof(GetNonceAsync)}...");
+
+      if (state.Directory is not { NewNonce: { } newNonceUri })
+        return Result<string?>.InternalServerError(null, "Directory or NewNonce URL is null.");
+
+      var result = await _httpClient.SendAsync(new HttpRequestMessage(HttpMethod.Head, newNonceUri));
+
+      var nonce = result.Headers.GetValues(ReplayNonceHeader).FirstOrDefault();
+
+      if (nonce == null)
+        return Result<string?>.InternalServerError(null, "Nonce is null");
+
+      return Result<string?>.Ok(nonce);
+    }
+    catch (Exception ex) {
+      return HandleUnhandledException<string?>(ex);
+    }
+  }
+
+  private async Task<Result<SendResult<T>?>> SendAcmeRequest<T>(HttpRequestMessage request, State state, HttpMethod method) {
+    try {
+      var response = await _httpClient.SendAsync(request);
+
+      var responseText = await response.Content.ReadAsStringAsync();
+
+      HandleProblemResponseAsync(response, responseText);
+
+      var sendResult = ProcessResponseContent<T>(response, responseText);
+
+      return Result<SendResult<T>?>.Ok(sendResult);
+    }
+
+    catch (LetsEncrytException ex) {
+      return MapLetsEncryptException<SendResult<T>?>(state, ex, null);
+    }
+    catch (Exception ex) {
+      return HandleUnhandledException<SendResult<T>?>(ex);
+    }
+  }
+
+  private Result<string?> EncodeMessage(Guid sessionId, bool isPostAsGet, object? requestModel, ACMEJwsHeader protectedHeader) {
+    var state = GetOrCreateState(sessionId);
+
+    if (!state.TryGetAccountKey(out var rsa, out var jwk))
+      return Result<string?>.InternalServerError(AccountKeyMissingMessage);
+
+    if (isPostAsGet) {
+      if (!JwsGenerator.TryEncode(rsa, jwk, protectedHeader, out var jwsPostAsGet, out var errPostAsGet))
+        return Result<string?>.InternalServerError(errPostAsGet);
+
+      return Result<string?>.Ok(jwsPostAsGet.ToJson());
+    }
+
+    if (!JwsGenerator.TryEncode(rsa, jwk, protectedHeader, requestModel, out var jwsWithPayload, out var errWithPayload))
+      return Result<string?>.InternalServerError(errWithPayload);
+
+    return Result<string?>.Ok(jwsWithPayload.ToJson());
+  }
+
+  private static string GetContentType(ContentType type) => type.GetDisplayName();
+
+  private void PrepareRequestContent(HttpRequestMessage request, string json, HttpMethod method) {
+    request.Content = new StringContent(json ?? string.Empty);
+    var contentType = method == HttpMethod.Post
+      ? GetContentType(ContentType.JoseJson)
+      : GetContentType(ContentType.Json);
+    request.Content.Headers.ContentType = new MediaTypeHeaderValue(contentType);
+  }
+
+  private async Task<Result> PollChallengeStatus(Guid sessionId, AuthorizationChallengeChallenge challenge) {
+    if (challenge?.Url == null)
+      return Result.InternalServerError("Challenge URL is null");
+
+    var start = DateTime.UtcNow;
+
+    while (true) {
+      var pollRequest = new HttpRequestMessage(HttpMethod.Post, challenge.Url);
+
+      var nonceResult = await GetNonceAsync(sessionId, challenge.Url);
+      if (!nonceResult.IsSuccess || nonceResult.Value == null)
+        return nonceResult;
+
+      var nonce = nonceResult.Value;
+
+      var pollJsonResult = EncodeMessage(sessionId, true, null, new ACMEJwsHeader {
+        Url = challenge.Url.ToString(),
+        Nonce = nonce
+      });
+
+      if (!pollJsonResult.IsSuccess || pollJsonResult.Value == null)
+        return pollJsonResult;
+
+      var pollJson = pollJsonResult.Value;
+
+      PrepareRequestContent(pollRequest, pollJson, HttpMethod.Post);
+
+      var pollResponse = await _httpClient.SendAsync(pollRequest);
+
+      var pollResponseText = await pollResponse.Content.ReadAsStringAsync();
+
+      HandleProblemResponseAsync(pollResponse, pollResponseText);
+
+      var authChallenge = ProcessResponseContent<AuthorizationChallengeResponse>(pollResponse, pollResponseText);
+
+      if (authChallenge.Result?.Status != "pending")
+        return authChallenge.Result?.Status == "valid" ? Result.Ok() : Result.InternalServerError();
+
+      if ((DateTime.UtcNow - start).Seconds > 120)
+        return Result.InternalServerError("Timeout");
+
+      await Task.Delay(1000);
+    }
+  }
+
+  private void HandleProblemResponseAsync(HttpResponseMessage response, string responseText) {
+    if (response.Content.Headers.ContentType?.MediaType == GetContentType(ContentType.ProblemJson)) {
+      var problem = responseText.ToObject<Problem>();
+
+      throw new LetsEncrytException(problem, response);
+    }
+
+    if (response.Content.Headers.ContentType?.MediaType == GetContentType(ContentType.Json)) {
+      var authorizationChallengeChallenge = responseText.ToObject<AuthorizationChallengeChallenge>();
+
+      if (authorizationChallengeChallenge?.Status == "invalid") {
+        throw new LetsEncrytException(new Problem {
+          Type = authorizationChallengeChallenge.Error?.Type,
+          Detail = authorizationChallengeChallenge.Error?.Detail,
+          RawJson = responseText
+        }, response);
+      }
+    }
+  }
+
+  private SendResult<TResult> ProcessResponseContent<TResult>(HttpResponseMessage response, string responseText) {
+    if (response.Content.Headers.ContentType?.MediaType == GetContentType(ContentType.PemCertificateChain) && typeof(TResult) == typeof(string)) {
+      return new SendResult<TResult> {
+        Result = (TResult)(object)responseText
+      };
+    }
+    var responseContent = responseText.ToObject<TResult>();
+    if (responseContent is IHasLocation ihl && response.Headers.Location != null) {
+      ihl.Location = response.Headers.Location;
+    }
+    return new SendResult<TResult> {
+      Result = responseContent,
+      ResponseText = responseText
+    };
+  }
+
+  private static bool StatusEquals(string? status, OrderStatus expected) => status == expected.GetDisplayName();
+
+  private Result MapLetsEncryptException(State state, LetsEncrytException ex) =>
+    MapLetsEncryptExceptionCore<Result>(state, ex, m => Result.TooManyRequests(m), m => Result.InternalServerError(m));
+
+  private Result<T?> MapLetsEncryptException<T>(State state, LetsEncrytException ex, T? defaultValue) =>
+    MapLetsEncryptExceptionCore(state, ex, m => Result<T?>.TooManyRequests(defaultValue, m), m => Result<T?>.InternalServerError(defaultValue, m));
+
+  private TResult MapLetsEncryptExceptionCore<TResult>(
+      State state,
+      LetsEncrytException ex,
+      Func<string, TResult> tooManyRequests,
+      Func<string, TResult> internalError) {
+    try {
+      if (ex.ProblemKind == AcmeProblemKind.RateLimited) {
+        var when = ex.RetryAfterUtc ?? DateTimeOffset.UtcNow.AddHours(1);
+        var id = ex.RateLimitedIdentifier;
+        if (state.Cache != null && !string.IsNullOrEmpty(id)) {
+          var key = id.ToLowerInvariant();
+          state.Cache.AcmeRenewalNotBeforeUtcByHostname ??= new Dictionary<string, DateTimeOffset>(StringComparer.OrdinalIgnoreCase);
+          if (state.Cache.AcmeRenewalNotBeforeUtcByHostname.TryGetValue(key, out var existing))
+            when = when > existing ? when : existing;
+          state.Cache.AcmeRenewalNotBeforeUtcByHostname[key] = when;
+        }
+
+        _logger.LogWarning(
+            "ACME rate limited: Kind {AcmeProblemKind}, Type {AcmeProblemType}, Hostname {Hostname}, RetryNotBefore {RetryNotBeforeUtc:o}. Detail: {Detail}",
+            ex.ProblemKind, ex.Problem?.Type, id, when, ex.Problem?.Detail);
+
+        var msg = string.IsNullOrEmpty(id)
+          ? $"Let's Encrypt rate limit. Do not retry certificate operations before {when:u} UTC."
+          : $"Let's Encrypt rate limit for hostname '{id}'. Do not retry before {when:u} UTC.";
+        return tooManyRequests(msg);
+      }
+
+      _logger.LogWarning(ex,
+          "Let's Encrypt ACME problem: Kind {AcmeProblemKind}, Type {AcmeProblemType}. {Detail}",
+          ex.ProblemKind, ex.Problem?.Type, ex.Problem?.Detail);
+      var fallback = string.IsNullOrEmpty(ex.Message) ? "Let's Encrypt request failed." : ex.Message;
+      return internalError(fallback);
+    }
+    finally {
+      ex.Response?.Dispose();
+    }
+  }
+
+  private Result HandleUnhandledException(Exception ex, string defaultMessage = "Let's Encrypt client unhandled exception") {
+    _logger.LogError(ex, defaultMessage);
+    return Result.InternalServerError([defaultMessage, .. ex.ExtractMessages()]);
+  }
+
+  private Result<T?> HandleUnhandledException<T>(Exception ex, T? defaultValue = default, string defaultMessage = "Let's Encrypt client unhandled exception") {
+    _logger.LogError(ex, defaultMessage);
+    return Result<T?>.InternalServerError(defaultValue, [.. ex.ExtractMessages()]);
+  }
+  #endregion
+}

src/LetsEncrypt/Services/LetsEncryptService.cs

@@ -15,7 +15,6 @@ using MaksIT.LetsEncrypt.Models.Interfaces;
 using MaksIT.LetsEncrypt.Models.Requests;
 using MaksIT.LetsEncrypt.Models.Responses;
 using MaksIT.Results;
-using Microsoft.Extensions.Caching.Memory;
 using Microsoft.Extensions.Logging;
 using System.Net.Http.Headers;
 using System.Security.Cryptography;
@@ -37,32 +36,33 @@ public interface ILetsEncryptService {
   Task<Result> RevokeCertificate(Guid sessionId, string subject, RevokeReason reason);
 }
 
-public class LetsEncryptService : ILetsEncryptService {
+public partial class LetsEncryptService : ILetsEncryptService {
   private const string DnsType = "dns";
   private const string DirectoryEndpoint = "directory";
   private const string ReplayNonceHeader = "Replay-Nonce";
+  private const string AccountKeyMissingMessage = "Account key is not loaded; complete Init before this operation.";
 
   private readonly ILogger<LetsEncryptService> _logger;
   private readonly LetsEncryptConfiguration _appSettings;
   private readonly HttpClient _httpClient;
-  private readonly IMemoryCache _memoryCache;
+  private readonly AcmeSessionStore _sessions;
 
   public LetsEncryptService(
       ILogger<LetsEncryptService> logger,
       LetsEncryptConfiguration appSettings,
       HttpClient httpClient,
-      IMemoryCache cache
+      AcmeSessionStore sessions
    ) {
     _logger = logger;
     _appSettings = appSettings;
     _httpClient = httpClient;
-    _memoryCache = cache;
+    _sessions = sessions;
   }
 
   public Result<RegistrationCache?> GetRegistrationCache(Guid sessionId) {
     var state = GetOrCreateState(sessionId);
 
-    if (state?.Cache == null)
+    if (state.Cache == null)
       return Result<RegistrationCache?>.InternalServerError(null);
 
     return Result<RegistrationCache?>.Ok(state.Cache);
@@ -92,7 +92,8 @@ public class LetsEncryptService : ILetsEncryptService {
       return Result.Ok("Client configured successfully.");
     }
     catch (LetsEncrytException ex) {
-      return HandleUnhandledException(ex, "Let's Encrypt client encountered a problem");
+      var state = GetOrCreateState(sessionId);
+      return MapLetsEncryptException(state, ex);
     }
     catch (Exception ex) {
       return HandleUnhandledException(ex);
@@ -149,21 +150,24 @@ public class LetsEncryptService : ILetsEncryptService {
         state.Rsa = accountKey;
         state.Jwk = jwk;
 
+        if (state.Directory.NewAccount is not { } newAccountUri)
+          return Result.InternalServerError("Directory is missing NewAccount URL.");
+
         var letsEncryptOrder = new Account {
           TermsOfServiceAgreed = true,
           Contacts = [.. contacts.Select(contact => $"mailto:{contact}")]
         };
 
-        var request = new HttpRequestMessage(HttpMethod.Post, state.Directory.NewAccount);
+        var request = new HttpRequestMessage(HttpMethod.Post, newAccountUri);
 
-        var nonceResult = await GetNonceAsync(sessionId, state.Directory.NewAccount);
+        var nonceResult = await GetNonceAsync(sessionId, newAccountUri);
         if (!nonceResult.IsSuccess || nonceResult.Value == null)
           return nonceResult;
 
         var nonce = nonceResult.Value;
 
         var jsonResult = EncodeMessage(sessionId, false, letsEncryptOrder, new ACMEJwsHeader {
-          Url = state.Directory.NewAccount.ToString(),
+          Url = newAccountUri.ToString(),
           Nonce = nonce
         });
 
@@ -183,9 +187,9 @@ public class LetsEncryptService : ILetsEncryptService {
         state.Jwk.KeyId = result.Result?.Location?.ToString() ?? string.Empty;
 
         if (result.Result?.Status != "valid") {
-          errorMessage = $"Account status is not valid, was: {result.Result?.Status} \r\n {result.ResponseText}";
+          var accountStatusMessage = $"Account status is not valid, was: {result.Result?.Status} \r\n {result.ResponseText}";
-          _logger.LogError(errorMessage);
+          _logger.LogError(accountStatusMessage);
-          return Result.InternalServerError(errorMessage);
+          return Result.InternalServerError(accountStatusMessage);
         }
 
         state.Cache = new RegistrationCache {
@@ -204,7 +208,7 @@ public class LetsEncryptService : ILetsEncryptService {
       return Result.Ok("Initialization successful.");
     }
     catch (LetsEncrytException ex) {
-      return HandleUnhandledException(ex, "Let's Encrypt client encountered a problem");
+      return MapLetsEncryptException(state, ex);
     }
     catch (Exception ex) {
       return HandleUnhandledException(ex);
@@ -248,19 +252,19 @@ public class LetsEncryptService : ILetsEncryptService {
         }).ToArray() ?? []
       };
 
-      if (state.Directory == null || state.Directory.NewOrder == null)
+      if (state.Directory?.NewOrder is not { } newOrderUri)
         return Result<Dictionary<string, string>?>.InternalServerError(null);
 
-      var request = new HttpRequestMessage(HttpMethod.Post, state.Directory.NewOrder);
+      var request = new HttpRequestMessage(HttpMethod.Post, newOrderUri);
 
-      var nonceResult = await GetNonceAsync(sessionId, state.Directory.NewOrder);
+      var nonceResult = await GetNonceAsync(sessionId, newOrderUri);
       if (!nonceResult.IsSuccess || nonceResult.Value == null)
         return nonceResult.ToResultOfType<Dictionary<string, string>?>(_ => null);
 
       var nonce = nonceResult.Value;
 
       var jsonResult = EncodeMessage(sessionId, false, letsEncryptOrder, new ACMEJwsHeader {
-        Url = state.Directory.NewOrder.ToString(),
+        Url = newOrderUri.ToString(),
         Nonce = nonce
       });
 
@@ -323,7 +327,7 @@ public class LetsEncryptService : ILetsEncryptService {
           continue;
 
         if (!StatusEquals(challengeResponse.Result?.Status, OrderStatus.Pending)) {
-          _logger.LogError($"Expected authorization status '{OrderStatus.Pending.GetDisplayName()}', but got: {state.CurrentOrder?.Status} \r\n {challengeResponse.ResponseText}");
+          _logger.LogError($"Expected authorization status '{OrderStatus.Pending.GetDisplayName()}', but got: {challengeResponse.Result?.Status} \r\n {challengeResponse.ResponseText}");
           return Result<Dictionary<string, string>?>.InternalServerError(null);
         }
 
@@ -340,6 +344,9 @@ public class LetsEncryptService : ILetsEncryptService {
         if (state.Cache != null)
           state.Cache.ChallengeType = challengeType;
 
+        if (state.Jwk is null)
+          return Result<Dictionary<string, string>?>.InternalServerError(null, AccountKeyMissingMessage);
+
         if (!JwkThumbprintUtility.TryGetKeyAuthorization(state.Jwk, challenge.Token, out var keyToken, out var errorMessage))
           return Result<Dictionary<string, string>?>.InternalServerError(null, errorMessage);
 
@@ -381,7 +388,12 @@ public class LetsEncryptService : ILetsEncryptService {
       for (var index = 0; index < state.Challenges.Count; index++) {
         var challenge = state.Challenges[index];
 
-        if (challenge?.Url == null) {
+        if (challenge is null) {
+          _logger.LogError("Challenge entry is null");
+          return Result.InternalServerError("Challenge entry is null");
+        }
+
+        if (challenge.Url is null) {
           _logger.LogError("Challenge URL is null");
           return Result.InternalServerError("Challenge URL is null");
         }
@@ -406,7 +418,7 @@ public class LetsEncryptService : ILetsEncryptService {
 
         PrepareRequestContent(request, json, HttpMethod.Post);
 
-        var authChallenge = await SendAcmeRequest<AuthorizationChallengeResponse>(request, state, HttpMethod.Post);
+        _ = await SendAcmeRequest<AuthorizationChallengeResponse>(request, state, HttpMethod.Post);
 
         var result = await PollChallengeStatus(sessionId, challenge);
 
@@ -415,6 +427,9 @@ public class LetsEncryptService : ILetsEncryptService {
       }
       return Result.Ok();
     }
+    catch (LetsEncrytException ex) {
+      return MapLetsEncryptException(GetOrCreateState(sessionId), ex);
+    }
     catch (Exception ex) {
       return HandleUnhandledException(ex);
     }
@@ -428,24 +443,27 @@ public class LetsEncryptService : ILetsEncryptService {
 
       var state = GetOrCreateState(sessionId);
 
+      if (state.Directory?.NewOrder is not { } newOrderUri)
+        return Result.InternalServerError("Directory is not configured. Run ConfigureClient first.");
+
       var letsEncryptOrder = new Order {
         Expires = DateTime.UtcNow.AddDays(2),
         Identifiers = hostnames?.Where(h => h != null).Select(hostname => new OrderIdentifier {
-          Type = "dns",
+          Type = DnsType,
           Value = hostname!
         }).ToArray() ?? []
       };
 
-      var request = new HttpRequestMessage(HttpMethod.Post, state.Directory!.NewOrder);
+      var request = new HttpRequestMessage(HttpMethod.Post, newOrderUri);
 
-      var nonceResult = await GetNonceAsync(sessionId, state.Directory.NewOrder);
+      var nonceResult = await GetNonceAsync(sessionId, newOrderUri);
       if (!nonceResult.IsSuccess || nonceResult.Value == null)
         return nonceResult;
 
       var nonce = nonceResult.Value;
 
       var jsonResult = EncodeMessage(sessionId, false, letsEncryptOrder, new ACMEJwsHeader {
-        Url = state.Directory.NewOrder.ToString(),
+        Url = newOrderUri.ToString(),
         Nonce = nonce
       });
 
@@ -479,15 +497,14 @@ public class LetsEncryptService : ILetsEncryptService {
 
       _logger.LogInformation($"Executing {nameof(GetCertificate)}...");
 
-      if (state.CurrentOrder?.Identifiers == null) {
+      if (state.CurrentOrder?.Identifiers is not { } initialIdentifiers)
         return Result.InternalServerError();
-      }
 
       var key = new RSACryptoServiceProvider(4096);
       var csr = new CertificateRequest("CN=" + subject, key, HashAlgorithmName.SHA256, RSASignaturePadding.Pkcs1);
       var san = new SubjectAlternativeNameBuilder();
 
-      foreach (var host in state.CurrentOrder.Identifiers) {
+      foreach (var host in initialIdentifiers) {
         if (host?.Value != null)
           san.AddDnsName(host.Value);
       }
@@ -503,23 +520,34 @@ public class LetsEncryptService : ILetsEncryptService {
       var start = DateTime.UtcNow;
 
       while (certificateUrl == null) {
-        var hostnames = state.CurrentOrder?.Identifiers?.Select(x => x?.Value).Where(x => x != null).Cast<string>().ToArray() ?? [];
+        var activeOrder = state.CurrentOrder;
+        if (activeOrder?.Identifiers is not { } idents)
+          return Result.InternalServerError("Current order identifiers are not available.");
+
+        var hostnames = idents.Select(x => x?.Value).Where(x => x != null).Cast<string>().ToArray();
 
         await GetOrder(sessionId, hostnames);
 
-        var status = state.CurrentOrder?.Status;
+        activeOrder = state.CurrentOrder;
+        if (activeOrder is null)
+          return Result.InternalServerError("Current order is no longer available.");
+
+        var status = activeOrder.Status;
 
         if (StatusEquals(status, OrderStatus.Ready)) {
-          var request = new HttpRequestMessage(HttpMethod.Post, state.CurrentOrder.Finalize);
+          if (activeOrder.Finalize is not { } finalizeUri)
+            return Result.InternalServerError("Order finalize URL is missing.");
 
-          var nonceResult = await GetNonceAsync(sessionId, state.CurrentOrder.Finalize);
+          var request = new HttpRequestMessage(HttpMethod.Post, finalizeUri);
+
+          var nonceResult = await GetNonceAsync(sessionId, finalizeUri);
           if (!nonceResult.IsSuccess || nonceResult.Value == null)
             return nonceResult;
 
           var nonce = nonceResult.Value;
 
           var jsonResult = EncodeMessage(sessionId, false, letsEncryptOrder, new ACMEJwsHeader {
-            Url = state.CurrentOrder.Finalize.ToString(),
+            Url = finalizeUri.ToString(),
             Nonce = nonce
           });
 
@@ -537,16 +565,20 @@ public class LetsEncryptService : ILetsEncryptService {
           var order = orderResult.Value;
 
           if (StatusEquals(order.Result?.Status, OrderStatus.Processing)) {
-            request = new HttpRequestMessage(HttpMethod.Post, state.CurrentOrder.Location!);
+            activeOrder = state.CurrentOrder;
+            if (activeOrder?.Location is not { } orderLocation)
+              return Result.InternalServerError("Order location URL is missing.");
 
-            nonceResult = await GetNonceAsync(sessionId, state.CurrentOrder.Location);
+            request = new HttpRequestMessage(HttpMethod.Post, orderLocation);
+
+            nonceResult = await GetNonceAsync(sessionId, orderLocation);
             if (!nonceResult.IsSuccess || nonceResult.Value == null)
               return nonceResult;
 
             nonce = nonceResult.Value;
 
             jsonResult = EncodeMessage(sessionId, true, null, new ACMEJwsHeader {
-              Url = state.CurrentOrder.Location.ToString(),
+              Url = orderLocation.ToString(),
               Nonce = nonce
             });
 
@@ -565,11 +597,15 @@ public class LetsEncryptService : ILetsEncryptService {
           }
 
           if (StatusEquals(order.Result?.Status, OrderStatus.Valid)) {
-            certificateUrl = order.Result.Certificate;
+            certificateUrl = order.Result?.Certificate;
+            if (certificateUrl is null)
+              return Result.InternalServerError("Certificate URL was not returned by the CA.");
           }
         }
         else if (StatusEquals(status, OrderStatus.Valid)) {
-          certificateUrl = state.CurrentOrder.Certificate;
+          if (activeOrder.Certificate is not { } certUri)
+            return Result.InternalServerError("Certificate URL is missing on the order.");
+          certificateUrl = certUri;
           break;
         }
 
@@ -579,7 +615,10 @@ public class LetsEncryptService : ILetsEncryptService {
         await Task.Delay(1000);
       }
 
-      var finalRequest = new HttpRequestMessage(HttpMethod.Post, certificateUrl!);
+      if (certificateUrl is null)
+        return Result.InternalServerError("Certificate URL could not be determined.");
+
+      var finalRequest = new HttpRequestMessage(HttpMethod.Post, certificateUrl);
 
       var finalNonceResult = await GetNonceAsync(sessionId, certificateUrl);
       if (!finalNonceResult.IsSuccess || finalNonceResult.Value == null)
@@ -618,14 +657,13 @@ public class LetsEncryptService : ILetsEncryptService {
         PrivatePem = key.ExportRSAPrivateKeyPem()
       };
 
-      var certPem = pem.Result ?? string.Empty;
+      state.Cache.ClearAcmeCooldownForHostname(subject);
-
-      if (!string.IsNullOrEmpty(certPem)) {
-        var cert = new X509Certificate2(Encoding.UTF8.GetBytes(certPem));
-      }
 
       return Result.Ok();
     }
+    catch (LetsEncrytException ex) {
+      return MapLetsEncryptException(GetOrCreateState(sessionId), ex);
+    }
     catch (Exception ex) {
       return HandleUnhandledException(ex);
     }
@@ -657,7 +695,7 @@ public class LetsEncryptService : ILetsEncryptService {
         return Result.InternalServerError("Certificate PEM is null or empty");
       }
 
-      var certificate = new X509Certificate2(Encoding.UTF8.GetBytes(certPem));
+      var certificate = X509Certificate2.CreateFromPem(certPem);
       
       var derEncodedCert = certificate.Export(X509ContentType.Cert);
       
@@ -668,20 +706,26 @@ public class LetsEncryptService : ILetsEncryptService {
         Reason = (int)reason
       };
 
-      var request = new HttpRequestMessage(HttpMethod.Post, state.Directory!.RevokeCert);
+      if (state.Directory?.RevokeCert is not { } revokeUri)
+        return Result.InternalServerError("Directory is not configured or RevokeCert URL is missing.");
 
-      var nonceResult = await GetNonceAsync(sessionId, state.Directory.RevokeCert);
+      if (!state.TryGetAccountKey(out var rsa, out var jwk))
+        return Result.InternalServerError(AccountKeyMissingMessage);
+
+      var request = new HttpRequestMessage(HttpMethod.Post, revokeUri);
+
+      var nonceResult = await GetNonceAsync(sessionId, revokeUri);
       if (!nonceResult.IsSuccess || nonceResult.Value == null)
         return nonceResult;
 
       var nonce = nonceResult.Value;
 
       var jwsHeader = new ACMEJwsHeader {
-        Url = state.Directory.RevokeCert.ToString(),
+        Url = revokeUri.ToString(),
         Nonce = nonce
       };
 
-      if (!JwsGenerator.TryEncode(state.Rsa, state.Jwk, jwsHeader, revokeRequest, out var jwsMessage, out var errorMessage)) {
+      if (!JwsGenerator.TryEncode(rsa, jwk, jwsHeader, revokeRequest, out var jwsMessage, out var errorMessage)) {
         return Result.InternalServerError(errorMessage);
       }
 
@@ -695,203 +739,29 @@ public class LetsEncryptService : ILetsEncryptService {
 
       var responseText = await response.Content.ReadAsStringAsync();
 
-      if (response.Content.Headers.ContentType?.MediaType == GetContentType(ContentType.ProblemJson)) {
+      HandleProblemResponseAsync(response, responseText);
-        var erroObj = responseText.ToObject<Problem>();
-      }
 
+      try {
         if (!response.IsSuccessStatusCode)
-        Result.InternalServerError(responseText);
+          return Result.InternalServerError(responseText);
 
         state.Cache.CachedCerts.Remove(subject);
         _logger.LogInformation("Certificate revoked successfully");
 
         return Result.Ok();
+      }
+      finally {
+        response.Dispose();
+      }
 
     }
+    catch (LetsEncrytException ex) {
+      var state = GetOrCreateState(sessionId);
+      return MapLetsEncryptException(state, ex);
+    }
     catch (Exception ex) {
       return HandleUnhandledException(ex);
     }
   }
   #endregion
-
-  #region Internal helpers
-  private State GetOrCreateState(Guid sessionId) {
-    if (!_memoryCache.TryGetValue(sessionId, out State? state) || state == null) {
-      state = new State();
-      _memoryCache.Set(sessionId, state, TimeSpan.FromHours(1));
-    }
-    return state;
-  }
-
-  private async Task<Result<string?>> GetNonceAsync(Guid sessionId, Uri uri) {
-    if (uri == null)
-      return Result<string?>.InternalServerError(null, "URI is null");
-
-    try {
-      var state = GetOrCreateState(sessionId);
-
-      _logger.LogInformation($"Executing {nameof(GetNonceAsync)}...");
-
-      if (state.Directory?.NewNonce == null)
-        return Result<string?>.InternalServerError(null, $"{nameof(state.Directory.NewNonce)} is null");
-
-      var result = await _httpClient.SendAsync(new HttpRequestMessage(HttpMethod.Head, state.Directory.NewNonce));
-
-      var nonce = result.Headers.GetValues("Replay-Nonce").FirstOrDefault();
-
-      if (nonce == null)
-        return Result<string?>.InternalServerError(null, "Nonce is null");
-
-      return Result<string?>.Ok(nonce);
-    }
-    catch (Exception ex) {
-      return HandleUnhandledException<string?>(ex);
-    }
-  }
-
-  // Helper: Send ACME request and process response
-  private async Task<Result<SendResult<T>?>> SendAcmeRequest<T>(HttpRequestMessage request, State state, HttpMethod method) {
-    try {
-      var response = await _httpClient.SendAsync(request);
-
-      var responseText = await response.Content.ReadAsStringAsync();
-
-      HandleProblemResponseAsync(response, responseText);
-
-      var sendResult = ProcessResponseContent<T>(response, responseText);
-
-      return Result<SendResult<T>?>.Ok(sendResult);
-    }
-
-    catch (Exception ex) {
-      return HandleUnhandledException<SendResult<T>?>(ex);
-    }
-  }
-
-  private Result<string?> EncodeMessage(Guid sessionId, bool isPostAsGet, object? requestModel, ACMEJwsHeader protectedHeader) {
-    var state = GetOrCreateState(sessionId);
-
-    JwsMessage jwsMessage;
-    string errorMessage;
-
-    if (isPostAsGet) {
-      if (!JwsGenerator.TryEncode(state.Rsa, state.Jwk, protectedHeader, out jwsMessage, out errorMessage))
-        return Result<string?>.InternalServerError(errorMessage);
-
-      return Result<string?>.Ok(jwsMessage.ToJson());
-    }
-    else {
-      if (!JwsGenerator.TryEncode(state.Rsa, state.Jwk, protectedHeader, requestModel, out jwsMessage, out errorMessage))
-        return Result<string?>.InternalServerError(errorMessage);
-
-      return Result<string?>.Ok(jwsMessage.ToJson());
-    }
-
-  }
-
-  private static string GetContentType(ContentType type) => type.GetDisplayName();
-
-  private void PrepareRequestContent(HttpRequestMessage request, string json, HttpMethod method) {
-    request.Content = new StringContent(json ?? string.Empty);
-    var contentType = method == HttpMethod.Post
-      ? GetContentType(ContentType.JoseJson)
-      : GetContentType(ContentType.Json);
-    request.Content.Headers.ContentType = new MediaTypeHeaderValue(contentType);
-  }
-
-  // Helper: Poll challenge status until valid or timeout
-  private async Task<Result> PollChallengeStatus(Guid sessionId, AuthorizationChallengeChallenge challenge) {
-    if (challenge?.Url == null)
-      return Result.InternalServerError("Challenge URL is null");
-
-    var start = DateTime.UtcNow;
-
-    while (true) {
-      var pollRequest = new HttpRequestMessage(HttpMethod.Post, challenge.Url);
-
-      var nonceResult = await GetNonceAsync(sessionId, challenge.Url);
-      if (!nonceResult.IsSuccess || nonceResult.Value == null)
-        return nonceResult;
-
-      var nonce = nonceResult.Value;
-
-      var pollJsonResult = EncodeMessage(sessionId, true, null, new ACMEJwsHeader {
-        Url = challenge.Url.ToString(),
-        Nonce = nonce
-      });
-
-      if (!pollJsonResult.IsSuccess || pollJsonResult.Value == null)
-        return pollJsonResult;
-
-      var pollJson = pollJsonResult.Value;
-
-      PrepareRequestContent(pollRequest, pollJson, HttpMethod.Post);
-
-      var pollResponse = await _httpClient.SendAsync(pollRequest);
-
-      var pollResponseText = await pollResponse.Content.ReadAsStringAsync();
-
-      HandleProblemResponseAsync(pollResponse, pollResponseText);
-
-      var authChallenge = ProcessResponseContent<AuthorizationChallengeResponse>(pollResponse, pollResponseText);
-
-      if (authChallenge.Result?.Status != "pending")
-        return authChallenge.Result?.Status == "valid" ? Result.Ok() : Result.InternalServerError();
-
-      if ((DateTime.UtcNow - start).Seconds > 120)
-        return Result.InternalServerError("Timeout");
-
-      await Task.Delay(1000);
-    }
-  }
-
-  private void HandleProblemResponseAsync(HttpResponseMessage response, string responseText) {
-    if (response.Content.Headers.ContentType?.MediaType == GetContentType(ContentType.ProblemJson)) {
-      var problem = responseText.ToObject<Problem>();
-
-      throw new LetsEncrytException(problem, response);
-    }
-
-    if (response.Content.Headers.ContentType?.MediaType == GetContentType(ContentType.Json)) {
-      var authorizationChallengeChallenge = responseText.ToObject<AuthorizationChallengeChallenge>();
-
-      if (authorizationChallengeChallenge?.Status == "invalid") {
-        throw new LetsEncrytException(new Problem {
-          Type = authorizationChallengeChallenge.Error.Type,
-          Detail = authorizationChallengeChallenge.Error.Detail,
-          RawJson = responseText
-        }, response);
-      }
-    }
-  }
-
-  private SendResult<TResult> ProcessResponseContent<TResult>(HttpResponseMessage response, string responseText) {
-    if (response.Content.Headers.ContentType?.MediaType == GetContentType(ContentType.PemCertificateChain) && typeof(TResult) == typeof(string)) {
-      return new SendResult<TResult> {
-        Result = (TResult)(object)responseText
-      };
-    }
-    var responseContent = responseText.ToObject<TResult>();
-    if (responseContent is IHasLocation ihl && response.Headers.Location != null) {
-      ihl.Location = response.Headers.Location;
-    }
-    return new SendResult<TResult> {
-      Result = responseContent,
-      ResponseText = responseText
-    };
-  }
-
-  // Helper for status comparison
-  private static bool StatusEquals(string? status, OrderStatus expected) => status == expected.GetDisplayName();
-
-  private Result HandleUnhandledException(Exception ex, string defaultMessage = "Let's Encrypt client unhandled exception") {
-    _logger.LogError(ex, defaultMessage);
-    return Result.InternalServerError([defaultMessage, .. ex.ExtractMessages()]);
-  }
-
-  private Result<T?> HandleUnhandledException<T>(Exception ex, T? defaultValue = default, string defaultMessage = "Let's Encrypt client unhandled exception") {
-    _logger.LogError(ex, defaultMessage);
-    return Result<T?>.InternalServerError(defaultValue, [.. ex.ExtractMessages()]);
-  }
-  #endregion
 }

src/MaksIT.Webapi/BackgroundServices/AutoRenewal.cs

@@ -71,14 +71,36 @@ namespace MaksIT.Webapi.BackgroundServices {
         return Result.Ok();
       }
 
+      var cooldownSkipped = new List<(string Hostname, DateTimeOffset NotBeforeUtc)>();
+      var eligible = new List<string>();
+      foreach (var hostname in toRenew) {
+        if (cache.IsHostnameInAcmeCooldown(hostname, out var notBefore)) {
+          cooldownSkipped.Add((hostname, notBefore));
+          continue;
+        }
+        eligible.Add(hostname);
+      }
+
+      if (cooldownSkipped.Count > 0) {
+        var sample = cooldownSkipped[0];
+        _logger.LogInformation(
+          "Skipping {SkippedCount} hostname(s) in ACME cooldown for account {AccountId} (e.g. {ExampleHost} until {NotBeforeUtc:u} UTC).",
+          cooldownSkipped.Count, cache.AccountId, sample.Hostname, sample.NotBeforeUtc);
+      }
+
+      if (!eligible.Any()) {
+        _logger.LogInformation("All due certificates for account {AccountId} are in ACME cooldown; no renewal attempted.", cache.AccountId);
+        return Result.Ok();
+      }
+
       var fullFlowResult = await _certsFlowService.FullFlow(
-          cache.IsStaging, cache.AccountId, cache.Description, cache.Contacts, cache.ChallengeType, toRenew.ToArray()
+          cache.IsStaging, cache.AccountId, cache.Description, cache.Contacts, cache.ChallengeType, eligible.ToArray()
       );
 
       if (!fullFlowResult.IsSuccess)
         return fullFlowResult;
 
-      _logger.LogInformation($"Certificates renewed for account {cache.AccountId}: {string.Join(", ", toRenew)}");
+      _logger.LogInformation("Certificates renewed for account {AccountId}: {Hostnames}", cache.AccountId, string.Join(", ", eligible));
 
       return Result.Ok();
     }

src/MaksIT.Webapi/MaksIT.Webapi.csproj

@@ -1,7 +1,7 @@
 <Project Sdk="Microsoft.NET.Sdk.Web">
 
   <PropertyGroup>
-    <Version>3.3.5</Version>
+    <Version>3.3.6</Version>
     <TargetFramework>net10.0</TargetFramework>
     <Nullable>enable</Nullable>
     <ImplicitUsings>enable</ImplicitUsings>

src/MaksIT.Webapi/Services/CertsFlowService.cs

@@ -187,28 +187,38 @@ public class CertsFlowService(
 
     var challengesResult = await NewOrderAsync(sessionId, hostnames, challengeType);
 
-    if (!challengesResult.IsSuccess)
+    if (!challengesResult.IsSuccess) {
+      await TryPersistRegistrationCacheFromSessionAsync(sessionId);
       return challengesResult.ToResultOfType<Guid?>(_ => null);
+    }
 
     if (challengesResult.Value?.Count > 0) {
       var challengeResult = await CompleteChallengesAsync(sessionId);
-      if (!challengeResult.IsSuccess)
+      if (!challengeResult.IsSuccess) {
+        await TryPersistRegistrationCacheFromSessionAsync(sessionId);
         return challengeResult.ToResultOfType<Guid?>(default);
       }
+    }
 
     var getOrderResult = await GetOrderAsync(sessionId, hostnames);
-    if (!getOrderResult.IsSuccess)
+    if (!getOrderResult.IsSuccess) {
+      await TryPersistRegistrationCacheFromSessionAsync(sessionId);
       return getOrderResult.ToResultOfType<Guid?>(default);
+    }
 
     var certsResult = await GetCertificatesAsync(sessionId, hostnames);
-    if (!certsResult.IsSuccess)
+    if (!certsResult.IsSuccess) {
+      await TryPersistRegistrationCacheFromSessionAsync(sessionId);
       return certsResult.ToResultOfType<Guid?>(default);
+    }
 
     if (!isStaging) {
       var applyCertsResult = await ApplyCertificatesAsync(accountId.Value);
-      if (!applyCertsResult.IsSuccess)
+      if (!applyCertsResult.IsSuccess) {
+        await TryPersistRegistrationCacheFromSessionAsync(sessionId);
         return applyCertsResult.ToResultOfType<Guid?>(_ => null);
       }
+    }
 
     return Result<Guid?>.Ok(initResult.Value);
   }
@@ -236,6 +246,16 @@ public class CertsFlowService(
     return Result<string?>.Ok(fileContent);
   }
 
+  private async Task TryPersistRegistrationCacheFromSessionAsync(Guid sessionId) {
+    var cacheResult = letsEncryptService.GetRegistrationCache(sessionId);
+    if (!cacheResult.IsSuccess || cacheResult.Value == null)
+      return;
+
+    var saveResult = await cacheService.SaveToCacheAsync(cacheResult.Value.AccountId, cacheResult.Value);
+    if (!saveResult.IsSuccess)
+      logger.LogWarning("Could not persist registration cache after ACME flow step for account {AccountId}.", cacheResult.Value.AccountId);
+  }
+
   private void DeleteExporedChallenges() {
     var currentDate = DateTime.Now;
     foreach (var file in Directory.GetFiles(_acmePath)) {