diff --git a/common/lib/dependabot/errors.rb b/common/lib/dependabot/errors.rb
index 69393d6e4b..1db1a2873d 100644
--- a/common/lib/dependabot/errors.rb
+++ b/common/lib/dependabot/errors.rb
@@ -83,6 +83,11 @@ def self.fetcher_error_details(error)
       # and responsibility for fixing it is on them, not us. As a result we
       # quietly log these as errors
       { "error-type": "server_error" }
+    when BadRequirementError
+      {
+        "error-type": "illformed_requirement",
+        "error-detail": { message: error.message }
+      }
     when *Octokit::RATE_LIMITED_ERRORS
       # If we get a rate-limited error we let dependabot-api handle the
       # retry by re-enqueing the update job after the reset
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli.Test/EntryPointTests.Analyze.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli.Test/EntryPointTests.Analyze.cs
index b5d08165d0..ef0799a4e4 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli.Test/EntryPointTests.Analyze.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli.Test/EntryPointTests.Analyze.cs
@@ -345,7 +345,8 @@ private static async Task RunAsync(
                     {
                         if (args[i] == "--job-path")
                         {
-                            experimentsManager = await ExperimentsManager.FromJobFileAsync(args[i + 1], new TestLogger());
+                            var experimentsResult = await ExperimentsManager.FromJobFileAsync(args[i + 1]);
+                            experimentsManager = experimentsResult.ExperimentsManager;
                         }
                     }
 
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli.Test/EntryPointTests.Discover.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli.Test/EntryPointTests.Discover.cs
index ad43a2292d..2622c56e85 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli.Test/EntryPointTests.Discover.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli.Test/EntryPointTests.Discover.cs
@@ -388,6 +388,83 @@ await RunAsync(path =>
             );
         }
 
+        [Fact]
+        public async Task JobFileParseErrorIsReported_InvalidJson()
+        {
+            using var testDirectory = new TemporaryDirectory();
+            var jobFilePath = Path.Combine(testDirectory.DirectoryPath, "job.json");
+            var resultFilePath = Path.Combine(testDirectory.DirectoryPath, DiscoveryWorker.DiscoveryResultFileName);
+            await File.WriteAllTextAsync(jobFilePath, "not json");
+            await RunAsync(path =>
+                [
+                    "discover",
+                    "--job-path",
+                    jobFilePath,
+                    "--repo-root",
+                    path,
+                    "--workspace",
+                    "/",
+                    "--output",
+                    resultFilePath
+                ],
+                initialFiles: [],
+                expectedResult: new()
+                {
+                    Path = "/",
+                    Projects = [],
+                    ErrorType = ErrorType.Unknown,
+                    ErrorDetailsPattern = "JsonException",
+                }
+            );
+        }
+
+        [Fact]
+        public async Task JobFileParseErrorIsReported_BadRequirement()
+        {
+            using var testDirectory = new TemporaryDirectory();
+            var jobFilePath = Path.Combine(testDirectory.DirectoryPath, "job.json");
+            var resultFilePath = Path.Combine(testDirectory.DirectoryPath, DiscoveryWorker.DiscoveryResultFileName);
+
+            // write a job file with a valid shape, but invalid requirement
+            await File.WriteAllTextAsync(jobFilePath, """
+                {
+                    "job": {
+                        "source": {
+                            "provider": "github",
+                            "repo": "test/repo"
+                        },
+                        "security-advisories": [
+                            {
+                                "dependency-name": "Some.Dependency",
+                                "affected-versions": ["not a valid requirement"]
+                            }
+                        ]
+                    }
+                }
+                """);
+            await RunAsync(path =>
+                [
+                    "discover",
+                    "--job-path",
+                    jobFilePath,
+                    "--repo-root",
+                    path,
+                    "--workspace",
+                    "/",
+                    "--output",
+                    resultFilePath
+                ],
+                initialFiles: [],
+                expectedResult: new()
+                {
+                    Path = "/",
+                    Projects = [],
+                    ErrorType = ErrorType.BadRequirement,
+                    ErrorDetailsPattern = "not a valid requirement",
+                }
+            );
+        }
+
         private static async Task RunAsync(
             Func<string, string[]> getArgs,
             TestFile[] initialFiles,
@@ -406,6 +483,7 @@ private static async Task RunAsync(
                 var originalErr = Console.Error;
                 Console.SetOut(writer);
                 Console.SetError(writer);
+                string? resultPath = null;
 
                 try
                 {
@@ -416,9 +494,15 @@ private static async Task RunAsync(
                     // manually pull out the experiments manager for the validate step below
                     for (int i = 0; i < args.Length - 1; i++)
                     {
-                        if (args[i] == "--job-path")
+                        switch (args[i])
                         {
-                            experimentsManager = await ExperimentsManager.FromJobFileAsync(args[i + 1], new TestLogger());
+                            case "--job-path":
+                                var experimentsResult = await ExperimentsManager.FromJobFileAsync(args[i + 1]);
+                                experimentsManager = experimentsResult.ExperimentsManager;
+                                break;
+                            case "--output":
+                                resultPath = args[i + 1];
+                                break;
                         }
                     }
 
@@ -434,7 +518,7 @@ private static async Task RunAsync(
                     Console.SetError(originalErr);
                 }
 
-                var resultPath = Path.Join(path, DiscoveryWorker.DiscoveryResultFileName);
+                resultPath ??= Path.Join(path, DiscoveryWorker.DiscoveryResultFileName);
                 var resultJson = await File.ReadAllTextAsync(resultPath);
                 var resultObject = JsonSerializer.Deserialize<WorkspaceDiscoveryResult>(resultJson, DiscoveryWorker.SerializerOptions);
                 return resultObject!;
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/AnalyzeCommand.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/AnalyzeCommand.cs
index 347c8adce4..0133b62b87 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/AnalyzeCommand.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/AnalyzeCommand.cs
@@ -29,7 +29,7 @@ internal static Command GetCommand(Action<int> setExitCode)
         command.SetHandler(async (jobPath, repoRoot, discoveryPath, dependencyPath, analysisDirectory) =>
         {
             var logger = new ConsoleLogger();
-            var experimentsManager = await ExperimentsManager.FromJobFileAsync(jobPath.FullName, logger);
+            var (experimentsManager, _errorResult) = await ExperimentsManager.FromJobFileAsync(jobPath.FullName);
             var worker = new AnalyzeWorker(experimentsManager, logger);
             await worker.RunAsync(repoRoot.FullName, discoveryPath.FullName, dependencyPath.FullName, analysisDirectory.FullName);
         }, JobPathOption, RepoRootOption, DiscoveryFilePathOption, DependencyFilePathOption, AnalysisFolderOption);
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/CloneCommand.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/CloneCommand.cs
index 581d95de0f..3a203b2895 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/CloneCommand.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/CloneCommand.cs
@@ -30,7 +30,7 @@ internal static Command GetCommand(Action<int> setExitCode)
             var apiHandler = new HttpApiHandler(apiUrl.ToString(), jobId);
             var logger = new ConsoleLogger();
             var gitCommandHandler = new ShellGitCommandHandler(logger);
-            var worker = new CloneWorker(apiHandler, gitCommandHandler, logger);
+            var worker = new CloneWorker(jobId, apiHandler, gitCommandHandler);
             var exitCode = await worker.RunAsync(jobPath, repoContentsPath);
             setExitCode(exitCode);
         }, JobPathOption, RepoContentsPathOption, ApiUrlOption, JobIdOption);
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/DiscoverCommand.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/DiscoverCommand.cs
index 1a11834cc5..d3d62b1a1e 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/DiscoverCommand.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/DiscoverCommand.cs
@@ -26,8 +26,22 @@ internal static Command GetCommand(Action<int> setExitCode)
 
         command.SetHandler(async (jobPath, repoRoot, workspace, outputPath) =>
         {
+            var (experimentsManager, errorResult) = await ExperimentsManager.FromJobFileAsync(jobPath.FullName);
+            if (errorResult is not null)
+            {
+                // to make testing easier, this should be a `WorkspaceDiscoveryResult` object
+                var discoveryErrorResult = new WorkspaceDiscoveryResult
+                {
+                    Path = workspace,
+                    Projects = [],
+                    ErrorType = errorResult.ErrorType,
+                    ErrorDetails = errorResult.ErrorDetails,
+                };
+                await DiscoveryWorker.WriteResultsAsync(repoRoot.FullName, outputPath.FullName, discoveryErrorResult);
+                return;
+            }
+
             var logger = new ConsoleLogger();
-            var experimentsManager = await ExperimentsManager.FromJobFileAsync(jobPath.FullName, logger);
             var worker = new DiscoveryWorker(experimentsManager, logger);
             await worker.RunAsync(repoRoot.FullName, workspace, outputPath.FullName);
         }, JobPathOption, RepoRootOption, WorkspaceOption, OutputOption);
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/RunCommand.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/RunCommand.cs
index 53d9ff4d2d..439c2b07d6 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/RunCommand.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/RunCommand.cs
@@ -33,12 +33,12 @@ internal static Command GetCommand(Action<int> setExitCode)
         command.SetHandler(async (jobPath, repoContentsPath, apiUrl, jobId, outputPath, baseCommitSha) =>
         {
             var apiHandler = new HttpApiHandler(apiUrl.ToString(), jobId);
+            var (experimentsManager, _errorResult) = await ExperimentsManager.FromJobFileAsync(jobPath.FullName);
             var logger = new ConsoleLogger();
-            var experimentsManager = await ExperimentsManager.FromJobFileAsync(jobPath.FullName, logger);
             var discoverWorker = new DiscoveryWorker(experimentsManager, logger);
             var analyzeWorker = new AnalyzeWorker(experimentsManager, logger);
             var updateWorker = new UpdaterWorker(experimentsManager, logger);
-            var worker = new RunWorker(apiHandler, discoverWorker, analyzeWorker, updateWorker, logger);
+            var worker = new RunWorker(jobId, apiHandler, discoverWorker, analyzeWorker, updateWorker, logger);
             await worker.RunAsync(jobPath, repoContentsPath, baseCommitSha, outputPath);
         }, JobPathOption, RepoContentsPathOption, ApiUrlOption, JobIdOption, OutputPathOption, BaseCommitShaOption);
 
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/UpdateCommand.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/UpdateCommand.cs
index 0b79b6da45..bd04c652cc 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/UpdateCommand.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Cli/Commands/UpdateCommand.cs
@@ -33,8 +33,8 @@ internal static Command GetCommand(Action<int> setExitCode)
 
         command.SetHandler(async (jobPath, repoRoot, solutionOrProjectFile, dependencyName, newVersion, previousVersion, isTransitive, resultOutputPath) =>
         {
+            var (experimentsManager, _errorResult) = await ExperimentsManager.FromJobFileAsync(jobPath.FullName);
             var logger = new ConsoleLogger();
-            var experimentsManager = await ExperimentsManager.FromJobFileAsync(jobPath.FullName, logger);
             var worker = new UpdaterWorker(experimentsManager, logger);
             await worker.RunAsync(repoRoot.FullName, solutionOrProjectFile.FullName, dependencyName, previousVersion, newVersion, isTransitive, resultOutputPath);
             setExitCode(0);
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Clone/CloneWorkerTests.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Clone/CloneWorkerTests.cs
index 71e6387bff..b658dc6f3f 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Clone/CloneWorkerTests.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Clone/CloneWorkerTests.cs
@@ -95,6 +95,65 @@ await TestCloneAsync(
         );
     }
 
+    [Fact]
+    public async Task JobFileParseErrorIsReported_InvalidJson()
+    {
+        // arrange
+        var testApiHandler = new TestApiHandler();
+        var testGitCommandHandler = new TestGitCommandHandler();
+        var cloneWorker = new CloneWorker("JOB-ID", testApiHandler, testGitCommandHandler);
+        using var testDirectory = new TemporaryDirectory();
+        var jobFilePath = Path.Combine(testDirectory.DirectoryPath, "job.json");
+        await File.WriteAllTextAsync(jobFilePath, "not json");
+
+        // act
+        var result = await cloneWorker.RunAsync(new FileInfo(jobFilePath), new DirectoryInfo(testDirectory.DirectoryPath));
+
+        // assert
+        Assert.Equal(1, result);
+        var expectedParseErrorObject = testApiHandler.ReceivedMessages.Single(m => m.Type == typeof(UnknownError));
+        var unknownError = (UnknownError)expectedParseErrorObject.Object;
+        Assert.Equal("JsonException", unknownError.Details["error-class"]);
+    }
+
+    [Fact]
+    public async Task JobFileParseErrorIsReported_BadRequirement()
+    {
+        // arrange
+        var testApiHandler = new TestApiHandler();
+        var testGitCommandHandler = new TestGitCommandHandler();
+        var cloneWorker = new CloneWorker("JOB-ID", testApiHandler, testGitCommandHandler);
+        using var testDirectory = new TemporaryDirectory();
+        var jobFilePath = Path.Combine(testDirectory.DirectoryPath, "job.json");
+
+        // write a job file with a valid shape, but invalid requirement
+        await File.WriteAllTextAsync(jobFilePath, """
+            {
+                "job": {
+                    "source": {
+                        "provider": "github",
+                        "repo": "test/repo"
+                    },
+                    "security-advisories": [
+                        {
+                            "dependency-name": "Some.Dependency",
+                            "affected-versions": ["not a valid requirement"]
+                        }
+                    ]
+                }
+            }
+            """);
+
+        // act
+        var result = await cloneWorker.RunAsync(new FileInfo(jobFilePath), new DirectoryInfo(testDirectory.DirectoryPath));
+
+        // assert
+        Assert.Equal(1, result);
+        var expectedParseErrorObject = testApiHandler.ReceivedMessages.Single(m => m.Type == typeof(BadRequirement));
+        var badRequirement = (BadRequirement)expectedParseErrorObject.Object;
+        Assert.Equal("not a valid requirement", badRequirement.Details["message"]);
+    }
+
     private class TestGitCommandHandlerWithOutputs : TestGitCommandHandler
     {
         private readonly string _stdout;
@@ -134,8 +193,7 @@ private static async Task TestCloneAsync(string provider, string repoMoniker, ob
         // arrange
         var testApiHandler = new TestApiHandler();
         testGitCommandHandler ??= new TestGitCommandHandler();
-        var testLogger = new TestLogger();
-        var worker = new CloneWorker(testApiHandler, testGitCommandHandler, testLogger);
+        var worker = new CloneWorker("TEST-JOB-ID", testApiHandler, testGitCommandHandler);
 
         // act
         var job = new Job()
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Discover/DiscoveryWorkerTestBase.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Discover/DiscoveryWorkerTestBase.cs
index 018729bd6c..4da255d04f 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Discover/DiscoveryWorkerTestBase.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Discover/DiscoveryWorkerTestBase.cs
@@ -45,7 +45,16 @@ protected static void ValidateWorkspaceResult(ExpectedWorkspaceDiscoveryResult e
         ValidateProjectResults(expectedResult.Projects, actualResult.Projects, experimentsManager);
         Assert.Equal(expectedResult.ExpectedProjectCount ?? expectedResult.Projects.Length, actualResult.Projects.Length);
         Assert.Equal(expectedResult.ErrorType, actualResult.ErrorType);
-        Assert.Equal(expectedResult.ErrorDetails, actualResult.ErrorDetails);
+        if (expectedResult.ErrorDetailsPattern is not null)
+        {
+            var errorDetails = actualResult.ErrorDetails?.ToString();
+            Assert.NotNull(errorDetails);
+            Assert.Matches(expectedResult.ErrorDetailsPattern, errorDetails);
+        }
+        else
+        {
+            Assert.Equal(expectedResult.ErrorDetails, actualResult.ErrorDetails);
+        }
 
         return;
 
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Discover/ExpectedDiscoveryResults.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Discover/ExpectedDiscoveryResults.cs
index 7e3638103f..d9d434aad6 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Discover/ExpectedDiscoveryResults.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Discover/ExpectedDiscoveryResults.cs
@@ -12,6 +12,7 @@ public record ExpectedWorkspaceDiscoveryResult : NativeResult
     public int? ExpectedProjectCount { get; init; }
     public ExpectedDependencyDiscoveryResult? GlobalJson { get; init; }
     public ExpectedDependencyDiscoveryResult? DotNetToolsJson { get; init; }
+    public string? ErrorDetailsPattern { get; init; } = null;
 }
 
 public record ExpectedSdkProjectDiscoveryResult : ExpectedDependencyDiscoveryResult
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Run/RunWorkerTests.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Run/RunWorkerTests.cs
index f02300e866..c58a29fcd7 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Run/RunWorkerTests.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Run/RunWorkerTests.cs
@@ -1733,7 +1733,7 @@ private static async Task RunAsync(Job job, TestFile[] files, IDiscoveryWorker?
         analyzeWorker ??= new AnalyzeWorker(experimentsManager, logger);
         updaterWorker ??= new UpdaterWorker(experimentsManager, logger);
 
-        var worker = new RunWorker(testApiHandler, discoveryWorker, analyzeWorker, updaterWorker, logger);
+        var worker = new RunWorker("TEST-JOB-ID", testApiHandler, discoveryWorker, analyzeWorker, updaterWorker, logger);
         var repoContentsPathDirectoryInfo = new DirectoryInfo(tempDirectory.DirectoryPath);
         var actualResult = await worker.RunAsync(job, repoContentsPathDirectoryInfo, "TEST-COMMIT-SHA");
         var actualApiMessages = testApiHandler.ReceivedMessages.ToArray();
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Run/SerializationTests.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Run/SerializationTests.cs
index 4d14c6c70f..5cbbedd511 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Run/SerializationTests.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core.Test/Run/SerializationTests.cs
@@ -1,6 +1,5 @@
 using NuGet.Versioning;
 
-using NuGetUpdater.Core.Analyze;
 using NuGetUpdater.Core.Run;
 using NuGetUpdater.Core.Run.ApiModel;
 using NuGetUpdater.Core.Test.Utilities;
@@ -228,37 +227,33 @@ public void DeserializeExperimentsManager_NoExperiments()
         Assert.False(experimentsManager.UseDirectDiscovery);
     }
 
-    [Fact]
-    public async Task DeserializeExperimentsManager_UnsupportedJobFileShape_InfoIsReportedAndEmptyExperimentSetIsReturned()
+    [Theory]
+    [MemberData(nameof(DeserializeErrorTypesData))]
+    public void SerializeError(JobErrorBase error, string expectedSerialization)
     {
-        // arrange
-        using var tempDir = new TemporaryDirectory();
-        var jobFilePath = Path.Combine(tempDir.DirectoryPath, "job.json");
-        var jobContent = """
-            {
-              "this-is-not-a-job-and-parsing-will-fail-but-an-empty-experiment-set-should-sill-be-returned": {
-              }
-            }
-            """;
-        await File.WriteAllTextAsync(jobFilePath, jobContent);
-        var capturingTestLogger = new CapturingTestLogger();
-
-        // act - this is the entrypoint the update command uses to parse the job file
-        var experimentsManager = await ExperimentsManager.FromJobFileAsync(jobFilePath, capturingTestLogger);
+        if (error is UnknownError unknown)
+        {
+            // special case the exception's call stack to make it testable
+            unknown.Details["error-backtrace"] = "TEST-BACKTRACE";
+        }
 
-        // assert
-        Assert.False(experimentsManager.UseLegacyDependencySolver);
-        Assert.False(experimentsManager.UseDirectDiscovery);
-        Assert.Single(capturingTestLogger.Messages, m => m.Contains("Error deserializing job file"));
+        var actual = HttpApiHandler.Serialize(error);
+        Assert.Equal(expectedSerialization, actual);
     }
 
     [Fact]
-    public void SerializeError()
+    public void SerializeError_AllErrorTypesHaveSerializationTests()
     {
-        var error = new JobRepoNotFound("some message");
-        var actual = HttpApiHandler.Serialize(error);
-        var expected = """{"data":{"error-type":"job_repo_not_found","error-details":{"message":"some message"}}}""";
-        Assert.Equal(expected, actual);
+        var untestedTypes = typeof(JobErrorBase).Assembly.GetTypes()
+            .Where(t => t.IsSubclassOf(typeof(JobErrorBase)))
+            .ToHashSet();
+        foreach (object?[] data in DeserializeErrorTypesData())
+        {
+            var testedErrorType = data[0]!.GetType();
+            untestedTypes.Remove(testedErrorType);
+        }
+
+        Assert.Empty(untestedTypes.Select(t => t.Name));
     }
 
     [Fact]
@@ -514,6 +509,57 @@ public void DeserializeCommitOptions()
         Assert.Null(jobWrapper.Job.CommitMessageOptions!.IncludeScope);
     }
 
+    public static IEnumerable<object?[]> DeserializeErrorTypesData()
+    {
+        yield return
+        [
+            new BadRequirement("some message"),
+            """
+            {"data":{"error-type":"illformed_requirement","error-details":{"message":"some message"}}}
+            """
+        ];
+
+        yield return
+        [
+            new DependencyFileNotFound("some message", "/some/file"),
+            """
+            {"data":{"error-type":"dependency_file_not_found","error-details":{"message":"some message","file-path":"/some/file"}}}
+            """
+        ];
+
+        yield return
+        [
+            new JobRepoNotFound("some message"),
+            """
+            {"data":{"error-type":"job_repo_not_found","error-details":{"message":"some message"}}}
+            """
+        ];
+
+        yield return
+        [
+            new PrivateSourceAuthenticationFailure(["url1", "url2"]),
+            """
+            {"data":{"error-type":"private_source_authentication_failure","error-details":{"source":"(url1|url2)"}}}
+            """
+        ];
+
+        yield return
+        [
+            new UnknownError(new Exception("some message"), "JOB-ID"),
+            """
+            {"data":{"error-type":"unknown_error","error-details":{"error-class":"Exception","error-message":"some message","error-backtrace":"TEST-BACKTRACE","package-manager":"nuget","job-id":"JOB-ID"}}}
+            """
+        ];
+
+        yield return
+        [
+            new UpdateNotPossible(["dep1", "dep2"]),
+            """
+            {"data":{"error-type":"update_not_possible","error-details":{"dependencies":["dep1","dep2"]}}}
+            """
+        ];
+    }
+
     public static IEnumerable<object?[]> DeserializeAllowedUpdatesData()
     {
         // common default value - most job files look like this
@@ -596,16 +642,4 @@ public void DeserializeCommitOptions()
             }
         ];
     }
-
-    private class CapturingTestLogger : ILogger
-    {
-        private readonly List<string> _messages = new();
-
-        public IReadOnlyList<string> Messages => _messages;
-
-        public void LogRaw(string message)
-        {
-            _messages.Add(message);
-        }
-    }
 }
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Analyze/RequirementConverter.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Analyze/RequirementConverter.cs
index 361643f67f..1da74d4326 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Analyze/RequirementConverter.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Analyze/RequirementConverter.cs
@@ -7,7 +7,20 @@ public class RequirementConverter : JsonConverter<Requirement>
 {
     public override Requirement? Read(ref Utf8JsonReader reader, Type typeToConvert, JsonSerializerOptions options)
     {
-        return Requirement.Parse(reader.GetString()!);
+        var text = reader.GetString();
+        if (text is null)
+        {
+            throw new ArgumentNullException(nameof(text));
+        }
+
+        try
+        {
+            return Requirement.Parse(text);
+        }
+        catch
+        {
+            throw new BadRequirementException(text);
+        }
     }
 
     public override void Write(Utf8JsonWriter writer, Requirement value, JsonSerializerOptions options)
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/BadRequirementException.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/BadRequirementException.cs
new file mode 100644
index 0000000000..1d9ffa78c2
--- /dev/null
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/BadRequirementException.cs
@@ -0,0 +1,9 @@
+namespace NuGetUpdater.Core;
+
+internal class BadRequirementException : Exception
+{
+    public BadRequirementException(string details)
+        : base(details)
+    {
+    }
+}
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Clone/CloneWorker.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Clone/CloneWorker.cs
index 761a364f77..4f48a8d477 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Clone/CloneWorker.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Clone/CloneWorker.cs
@@ -9,23 +9,45 @@ namespace NuGetUpdater.Core.Clone;
 
 public class CloneWorker
 {
+    private readonly string _jobId;
     private readonly IApiHandler _apiHandler;
     private readonly IGitCommandHandler _gitCommandHandler;
-    private readonly ILogger _logger;
 
-    public CloneWorker(IApiHandler apiHandler, IGitCommandHandler gitCommandHandler, ILogger logger)
+    public CloneWorker(string jobId, IApiHandler apiHandler, IGitCommandHandler gitCommandHandler)
     {
+        _jobId = jobId;
         _apiHandler = apiHandler;
         _gitCommandHandler = gitCommandHandler;
-        _logger = logger;
     }
 
     // entrypoint for cli
     public async Task<int> RunAsync(FileInfo jobFilePath, DirectoryInfo repoContentsPath)
     {
         var jobFileContent = await File.ReadAllTextAsync(jobFilePath.FullName);
-        var jobWrapper = RunWorker.Deserialize(jobFileContent);
-        var result = await RunAsync(jobWrapper.Job, repoContentsPath.FullName);
+
+        // only a limited set of errors can occur here
+        JobFile? jobFile = null;
+        JobErrorBase? parseError = null;
+        try
+        {
+            jobFile = RunWorker.Deserialize(jobFileContent);
+        }
+        catch (BadRequirementException ex)
+        {
+            parseError = new BadRequirement(ex.Message);
+        }
+        catch (Exception ex)
+        {
+            parseError = new UnknownError(ex, _jobId);
+        }
+
+        if (parseError is not null)
+        {
+            await ReportError(parseError);
+            return 1;
+        }
+
+        var result = await RunAsync(jobFile!.Job, repoContentsPath.FullName);
         return result;
     }
 
@@ -48,19 +70,24 @@ public async Task<int> RunAsync(Job job, string repoContentsPath)
         }
         catch (Exception ex)
         {
-            error = new UnknownError(ex.ToString());
+            error = new UnknownError(ex, _jobId);
         }
 
         if (error is not null)
         {
-            await _apiHandler.RecordUpdateJobError(error);
-            await _apiHandler.MarkAsProcessed(new("unknown"));
+            await ReportError(error);
             return 1;
         }
 
         return 0;
     }
 
+    private async Task ReportError(JobErrorBase error)
+    {
+        await _apiHandler.RecordUpdateJobError(error);
+        await _apiHandler.MarkAsProcessed(new("unknown"));
+    }
+
     internal static CommandArguments[] GetAllCommandArgs(Job job, string repoContentsPath)
     {
         var commandArgs = new List<CommandArguments>()
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Discover/DiscoveryWorker.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Discover/DiscoveryWorker.cs
index 398f04e54f..fdeaf75733 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Discover/DiscoveryWorker.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Discover/DiscoveryWorker.cs
@@ -57,6 +57,16 @@ internal async Task<WorkspaceDiscoveryResult> RunWithErrorHandlingAsync(string r
                 Projects = [],
             };
         }
+        catch (Exception ex)
+        {
+            result = new WorkspaceDiscoveryResult
+            {
+                ErrorType = ErrorType.Unknown,
+                ErrorDetails = ex.ToString(),
+                Path = workspacePath,
+                Projects = [],
+            };
+        }
 
         return result;
     }
@@ -397,6 +407,6 @@ internal static async Task WriteResultsAsync(string repoRootPath, string outputP
         }
 
         var resultJson = JsonSerializer.Serialize(result, SerializerOptions);
-        await File.WriteAllTextAsync(path: resultPath, resultJson);
+        await File.WriteAllTextAsync(resultPath, resultJson);
     }
 }
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/ErrorType.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/ErrorType.cs
index 36154ad039..23dab4bb8d 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/ErrorType.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/ErrorType.cs
@@ -4,6 +4,7 @@ public enum ErrorType
 {
     None,
     AuthenticationFailure,
+    BadRequirement,
     MissingFile,
     UpdateNotPossible,
     DependencyFileNotParseable,
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/ExperimentsManager.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/ExperimentsManager.cs
index 8e3cc01221..96a00680b7 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/ExperimentsManager.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/ExperimentsManager.cs
@@ -30,19 +30,42 @@ public static ExperimentsManager GetExperimentsManager(Dictionary<string, object
         };
     }
 
-    public static async Task<ExperimentsManager> FromJobFileAsync(string jobFilePath, ILogger logger)
+    public static async Task<(ExperimentsManager ExperimentsManager, NativeResult? ErrorResult)> FromJobFileAsync(string jobFilePath)
     {
-        var jobFileContent = await File.ReadAllTextAsync(jobFilePath);
+        var experimentsManager = new ExperimentsManager();
+        NativeResult? errorResult = null;
         try
         {
+            var jobFileContent = await File.ReadAllTextAsync(jobFilePath);
             var jobWrapper = RunWorker.Deserialize(jobFileContent);
-            return GetExperimentsManager(jobWrapper.Job.Experiments);
+            experimentsManager = GetExperimentsManager(jobWrapper.Job.Experiments);
+        }
+        catch (BadRequirementException ex)
+        {
+            errorResult = new NativeResult
+            {
+                ErrorType = ErrorType.BadRequirement,
+                ErrorDetails = ex.Message,
+            };
         }
         catch (JsonException ex)
         {
-            logger.Info($"Error deserializing job file: {ex.ToString()}: {jobFileContent}");
-            return new ExperimentsManager();
+            errorResult = new NativeResult
+            {
+                ErrorType = ErrorType.Unknown,
+                ErrorDetails = $"Error deserializing job file: {ex}: {File.ReadAllText(jobFilePath)}",
+            };
+        }
+        catch (Exception ex)
+        {
+            errorResult = new NativeResult
+            {
+                ErrorType = ErrorType.Unknown,
+                ErrorDetails = ex.ToString(),
+            };
         }
+
+        return (experimentsManager, errorResult);
     }
 
     private static bool IsEnabled(Dictionary<string, object>? experiments, string experimentName)
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/NuGetUpdater.Core.csproj b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/NuGetUpdater.Core.csproj
index d45ed65905..7bb1102c92 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/NuGetUpdater.Core.csproj
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/NuGetUpdater.Core.csproj
@@ -26,6 +26,7 @@
   </ItemGroup>
 
   <ItemGroup>
+    <InternalsVisibleTo Include="NuGetUpdater.Cli" />
     <InternalsVisibleTo Include="NuGetUpdater.Cli.Test" />
     <InternalsVisibleTo Include="NuGetUpdater.Core.Test" />
   </ItemGroup>
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/BadRequirement.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/BadRequirement.cs
new file mode 100644
index 0000000000..40cff22835
--- /dev/null
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/BadRequirement.cs
@@ -0,0 +1,10 @@
+namespace NuGetUpdater.Core.Run.ApiModel;
+
+public record BadRequirement : JobErrorBase
+{
+    public BadRequirement(string details)
+        : base("illformed_requirement")
+    {
+        Details["message"] = details;
+    }
+}
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/DependencyFileNotFound.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/DependencyFileNotFound.cs
index 94c1b71f08..91d385da47 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/DependencyFileNotFound.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/DependencyFileNotFound.cs
@@ -2,9 +2,10 @@ namespace NuGetUpdater.Core.Run.ApiModel;
 
 public record DependencyFileNotFound : JobErrorBase
 {
-    public DependencyFileNotFound(string filePath)
+    public DependencyFileNotFound(string message, string filePath)
         : base("dependency_file_not_found")
     {
-        Details = filePath;
+        Details["message"] = message;
+        Details["file-path"] = filePath;
     }
 }
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/JobErrorBase.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/JobErrorBase.cs
index 7507ba583d..3b38b43d3c 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/JobErrorBase.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/JobErrorBase.cs
@@ -13,6 +13,5 @@ public JobErrorBase(string type)
     public string Type { get; }
 
     [JsonPropertyName("error-details")]
-    [JsonIgnore(Condition = JsonIgnoreCondition.WhenWritingNull)]
-    public object? Details { get; init; } = null;
+    public Dictionary<string, object> Details { get; init; } = new();
 }
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/JobRepoNotFound.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/JobRepoNotFound.cs
index 12d9f229d7..3fd013426b 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/JobRepoNotFound.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/JobRepoNotFound.cs
@@ -5,9 +5,6 @@ public record JobRepoNotFound : JobErrorBase
     public JobRepoNotFound(string message)
         : base("job_repo_not_found")
     {
-        Details = new Dictionary<string, string>()
-        {
-            ["message"] = message
-        };
+        Details["message"] = message;
     }
 }
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/PrivateSourceAuthenticationFailure.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/PrivateSourceAuthenticationFailure.cs
index 35a39894fd..d8e5aeb49f 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/PrivateSourceAuthenticationFailure.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/PrivateSourceAuthenticationFailure.cs
@@ -5,6 +5,6 @@ public record PrivateSourceAuthenticationFailure : JobErrorBase
     public PrivateSourceAuthenticationFailure(string[] urls)
         : base("private_source_authentication_failure")
     {
-        Details = $"({string.Join("|", urls)})";
+        Details["source"] = $"({string.Join("|", urls)})";
     }
 }
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/UnknownError.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/UnknownError.cs
index 90517a8f1e..8773cc0817 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/UnknownError.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/UnknownError.cs
@@ -2,9 +2,13 @@ namespace NuGetUpdater.Core.Run.ApiModel;
 
 public record UnknownError : JobErrorBase
 {
-    public UnknownError(string details)
+    public UnknownError(Exception ex, string jobId)
         : base("unknown_error")
     {
-        Details = details;
+        Details["error-class"] = ex.GetType().Name;
+        Details["error-message"] = ex.Message;
+        Details["error-backtrace"] = ex.StackTrace ?? "<unknown>";
+        Details["package-manager"] = "nuget";
+        Details["job-id"] = jobId;
     }
 }
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/UpdateNotPossible.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/UpdateNotPossible.cs
index cdf7854063..6d0808240a 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/UpdateNotPossible.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/ApiModel/UpdateNotPossible.cs
@@ -5,6 +5,6 @@ public record UpdateNotPossible : JobErrorBase
     public UpdateNotPossible(string[] dependencies)
         : base("update_not_possible")
     {
-        Details = dependencies;
+        Details["dependencies"] = dependencies;
     }
 }
diff --git a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/RunWorker.cs b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/RunWorker.cs
index eb7a39cb65..43c82ce7e3 100644
--- a/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/RunWorker.cs
+++ b/nuget/helpers/lib/NuGetUpdater/NuGetUpdater.Core/Run/RunWorker.cs
@@ -12,6 +12,7 @@ namespace NuGetUpdater.Core.Run;
 
 public class RunWorker
 {
+    private readonly string _jobId;
     private readonly IApiHandler _apiHandler;
     private readonly ILogger _logger;
     private readonly IDiscoveryWorker _discoveryWorker;
@@ -25,8 +26,9 @@ public class RunWorker
         Converters = { new JsonStringEnumConverter(), new RequirementConverter(), new VersionConverter() },
     };
 
-    public RunWorker(IApiHandler apiHandler, IDiscoveryWorker discoverWorker, IAnalyzeWorker analyzeWorker, IUpdaterWorker updateWorker, ILogger logger)
+    public RunWorker(string jobId, IApiHandler apiHandler, IDiscoveryWorker discoverWorker, IAnalyzeWorker analyzeWorker, IUpdaterWorker updateWorker, ILogger logger)
     {
+        _jobId = jobId;
         _apiHandler = apiHandler;
         _logger = logger;
         _discoveryWorker = discoverWorker;
@@ -87,9 +89,13 @@ private async Task<RunResult> RunWithErrorHandlingAsync(Job job, DirectoryInfo r
         {
             error = new PrivateSourceAuthenticationFailure(lastUsedPackageSourceUrls);
         }
+        catch (BadRequirementException ex)
+        {
+            error = new BadRequirement(ex.Message);
+        }
         catch (MissingFileException ex)
         {
-            error = new DependencyFileNotFound(ex.FilePath);
+            error = new DependencyFileNotFound("file not found", ex.FilePath);
         }
         catch (UpdateNotPossibleException ex)
         {
@@ -97,7 +103,7 @@ private async Task<RunResult> RunWithErrorHandlingAsync(Job job, DirectoryInfo r
         }
         catch (Exception ex)
         {
-            error = new UnknownError(ex.ToString());
+            error = new UnknownError(ex, _jobId);
         }
 
         if (error is not null)
diff --git a/nuget/lib/dependabot/nuget/native_helpers.rb b/nuget/lib/dependabot/nuget/native_helpers.rb
index b40a353e04..2de499c279 100644
--- a/nuget/lib/dependabot/nuget/native_helpers.rb
+++ b/nuget/lib/dependabot/nuget/native_helpers.rb
@@ -301,6 +301,8 @@ def self.ensure_no_errors(json)
           raise DependencyFileNotParseable, T.must(T.let(error_details, T.nilable(String)))
         when "AuthenticationFailure"
           raise PrivateSourceAuthenticationFailure, T.let(error_details, T.nilable(String))
+        when "BadRequirement"
+          raise BadRequirementError, T.let(error_details, T.nilable(String))
         when "MissingFile"
           raise DependencyFileNotFound, T.let(error_details, T.nilable(String))
         when "UpdateNotPossible"