diff --git a/Tests/SwiftSDKGeneratorTests/EndToEndTests.swift b/Tests/SwiftSDKGeneratorTests/EndToEndTests.swift
index 8f67136..7365969 100644
--- a/Tests/SwiftSDKGeneratorTests/EndToEndTests.swift
+++ b/Tests/SwiftSDKGeneratorTests/EndToEndTests.swift
@@ -49,66 +49,80 @@ extension FileManager {
   }
 }
 
-final class EndToEndTests: XCTestCase {
-  private let testcases = [
-    #"""
-      // Default program generated by swift package init
-      print("Hello, world!")
-    """#,
-    #"""
-      // Check that libc_nonshared.a is linked properly
-      import Foundation
-
-      func fin() -> Void {
-        print("exiting")
-      }
-
-      atexit(fin)
-    """#,
-  ]
-
-  private let logger = Logger(label: "swift-sdk-generator")
-
-  // Building an SDK requires running the sdk-generator with `swift run swift-sdk-generator`.
-  // This takes a lock on `.build`, but if the tests are being run by `swift test` the outer Swift Package Manager
-  // instance will already hold this lock, causing the test to deadlock.   We can work around this by giving
-  // the `swift run swift-sdk-generator` instance its own scratch directory.
-  func buildSDK(inDirectory packageDirectory: FilePath, scratchPath: String, withArguments runArguments: String) async throws -> String {
-    let generatorOutput = try await Shell.readStdout(
-      "cd \(packageDirectory) && swift run --scratch-path \"\(scratchPath)\" swift-sdk-generator make-linux-sdk \(runArguments)"
-    )
-
-    let installCommand = try XCTUnwrap(generatorOutput.split(separator: "\n").first {
-      $0.contains("swift experimental-sdk install")
-    })
+// Building an SDK requires running the sdk-generator with `swift run swift-sdk-generator`.
+// This takes a lock on `.build`, but if the tests are being run by `swift test` the outer Swift Package Manager
+// instance will already hold this lock, causing the test to deadlock.   We can work around this by giving
+// the `swift run swift-sdk-generator` instance its own scratch directory.
+func buildSDK(_ logger: Logger, scratchPath: String, withArguments runArguments: String) async throws -> String {
+  var logger = logger
+  logger[metadataKey: "runArguments"] = "\"\(runArguments)\""
+  logger[metadataKey: "scratchPath"] = "\(scratchPath)"
+
+  logger.info("Building SDK")
+
+  var packageDirectory = FilePath(#filePath)
+  packageDirectory.removeLastComponent()
+  packageDirectory.removeLastComponent()
+
+  let generatorOutput = try await Shell.readStdout(
+    "cd \(packageDirectory) && swift run --scratch-path \"\(scratchPath)\" swift-sdk-generator make-linux-sdk \(runArguments)"
+  )
+  logger.info("Finished building SDK")
+
+  let installCommand = try XCTUnwrap(generatorOutput.split(separator: "\n").first {
+    $0.contains("swift experimental-sdk install")
+  })
+
+  let bundleName = try XCTUnwrap(
+    FilePath(String(XCTUnwrap(installCommand.split(separator: " ").last))).components.last
+  ).stem
+  logger[metadataKey: "bundleName"] = "\(bundleName)"
+
+  logger.info("Checking installed SDKs")
+  let installedSDKs = try await Shell.readStdout("swift experimental-sdk list").components(separatedBy: "\n")
+
+  // Make sure this bundle hasn't been installed already.
+  if installedSDKs.contains(bundleName) {
+    logger.info("Removing existing SDK")
+    try await Shell.run("swift experimental-sdk remove \(bundleName)")
+  }
 
-    let bundleName = try XCTUnwrap(
-      FilePath(String(XCTUnwrap(installCommand.split(separator: " ").last))).components.last
-    ).stem
+  logger.info("Installing new SDK")
+  let installOutput = try await Shell.readStdout(String(installCommand))
+  XCTAssertTrue(installOutput.contains("successfully installed"))
 
-    let installedSDKs = try await Shell.readStdout("swift experimental-sdk list").components(separatedBy: "\n")
+  return bundleName
+}
 
-    // Make sure this bundle hasn't been installed already.
-    if installedSDKs.contains(bundleName) {
-      try await Shell.run("swift experimental-sdk remove \(bundleName)")
+private let testcases = [
+  #"""
+    // Default program generated by swift package init
+    print("Hello, world!")
+  """#,
+  #"""
+    // Check that libc_nonshared.a is linked properly
+    import Foundation
+
+    func fin() -> Void {
+      print("exiting")
     }
 
-    let installOutput = try await Shell.readStdout(String(installCommand))
-    XCTAssertTrue(installOutput.contains("successfully installed"))
+    atexit(fin)
+  """#,
+]
 
-    return bundleName
-  }
+final class RepeatedBuildTests: XCTestCase {
+  private let logger = Logger(label: "swift-sdk-generator")
 
-  func testPackageInitExecutable() async throws {
+  func testRepeatedSDKBuilds() async throws {
     if ProcessInfo.processInfo.environment.keys.contains("JENKINS_URL") {
       throw XCTSkip("EndToEnd tests cannot currently run in CI: https://github.com/swiftlang/swift-sdk-generator/issues/145")
     }
 
-    var packageDirectory = FilePath(#filePath)
-    packageDirectory.removeLastComponent()
-    packageDirectory.removeLastComponent()
+    var logger = logger
+    logger[metadataKey: "testcase"] = "testRepeatedSDKBuilds"
 
-    // Do multiple runs with different sets of arguments.
+    // Test that an existing SDK can be rebuilt without cleaning up.
     // Test with no arguments by default:
     var possibleArguments = [""]
     do {
@@ -125,66 +139,268 @@ final class EndToEndTests: XCTestCase {
         continue
       }
 
-      let bundleName = try await FileManager.default.withTemporaryDirectory(logger: logger) { tempDir in
-        try await buildSDK(inDirectory: packageDirectory, scratchPath: tempDir.path, withArguments: runArguments)
+      try await FileManager.default.withTemporaryDirectory(logger: logger) { tempDir in
+        let _ = try await buildSDK(logger, scratchPath: tempDir.path, withArguments: runArguments)
+        let _ = try await buildSDK(logger, scratchPath: tempDir.path, withArguments: runArguments)
       }
+    }
+  }
+}
 
-      for testcase in self.testcases {
-        try await FileManager.default.withTemporaryDirectory(logger: logger) { tempDir in
-          let testPackageURL = tempDir.appendingPathComponent("swift-sdk-generator-test")
-          let testPackageDir = FilePath(testPackageURL.path)
-          try FileManager.default.createDirectory(atPath: testPackageDir.string, withIntermediateDirectories: true)
+// SDKConfiguration represents an SDK build configuration and can construct the corresponding SDK generator arguments
+struct SDKConfiguration {
+  var swiftVersion: String
+  var linuxDistributionName: String
+  var architecture: String
+  var withDocker: Bool
 
-          try await Shell.run("swift package --package-path \(testPackageDir) init --type executable")
-          let main_swift = testPackageURL.appendingPathComponent("Sources/main.swift")
-          try testcase.write(to: main_swift, atomically: true, encoding: .utf8)
+  var bundleName: String { "\(linuxDistributionName)_\(architecture)_\(swiftVersion)-RELEASE\(withDocker ? "_with-docker" : "")" }
 
-          var buildOutput = try await Shell.readStdout(
-            "swift build --package-path \(testPackageDir) --experimental-swift-sdk \(bundleName)"
-          )
-          XCTAssertTrue(buildOutput.contains("Build complete!"))
+  func withDocker(_ enabled: Bool = true) -> SDKConfiguration {
+    var res = self
+    res.withDocker = enabled
+    return res
+  }
 
-          try await Shell.run("rm -rf \(testPackageDir.appending(".build"))")
+  func withArchitecture(_ arch: String) -> SDKConfiguration {
+    var res = self
+    res.architecture = arch
+    return res
+  }
 
-          buildOutput = try await Shell.readStdout(
-            "swift build --package-path \(testPackageDir) --experimental-swift-sdk \(bundleName) --static-swift-stdlib"
-          )
-          XCTAssertTrue(buildOutput.contains("Build complete!"))
-        }
-      }
-    }
+  var sdkGeneratorArguments: String {
+    return [
+      "--sdk-name \(bundleName)",
+      withDocker ? "--with-docker" : nil,
+      "--swift-version \(swiftVersion)-RELEASE",
+      "--target \(architecture)-unknown-linux-gnu",
+      "--linux-distribution-name \(linuxDistributionName)"
+    ].compactMap{ $0 }.joined(separator: " ")
   }
+}
 
-  func testRepeatedSDKBuilds() async throws {
-    if ProcessInfo.processInfo.environment.keys.contains("JENKINS_URL") {
-      throw XCTSkip("EndToEnd tests cannot currently run in CI: https://github.com/swiftlang/swift-sdk-generator/issues/145")
-    }
+// Skip slow tests unless an environment variable is set
+func skipSlow() throws {
+  try XCTSkipUnless(
+    ProcessInfo.processInfo.environment.keys.contains("SWIFT_SDK_GENERATOR_RUN_SLOW_TESTS"),
+    "Skipping slow test because SWIFT_SDK_GENERATOR_RUN_SLOW_TESTS is not set"
+  )
+}
 
-    var packageDirectory = FilePath(#filePath)
-    packageDirectory.removeLastComponent()
-    packageDirectory.removeLastComponent()
+// Skip known failing tests unless an environment variable is set
+func skipBroken(_ message: String) throws {
+  try XCTSkipUnless(
+    ProcessInfo.processInfo.environment.keys.contains("SWIFT_SDK_GENERATOR_RUN_BROKEN_TESTS"),
+    "Skipping broken test because SWIFT_SDK_GENERATOR_RUN_BROKEN_TESTS is not set: \(message)"
+  )
+}
 
-    // Test that an existing SDK can be rebuilt without cleaning up.
-    // Test with no arguments by default:
-    var possibleArguments = [""]
+func buildTestcase(_ logger: Logger, testcase: String, bundleName: String, tempDir: URL) async throws {
+  let testPackageURL = tempDir.appendingPathComponent("swift-sdk-generator-test")
+  let testPackageDir = FilePath(testPackageURL.path)
+  try FileManager.default.createDirectory(atPath: testPackageDir.string, withIntermediateDirectories: true)
+
+  logger.info("Creating test project")
+  try await Shell.run("swift package --package-path \(testPackageDir) init --type executable")
+  let main_swift = testPackageURL.appendingPathComponent("Sources/main.swift")
+  try testcase.write(to: main_swift, atomically: true, encoding: .utf8)
+
+  logger.info("Building test project")
+  var buildOutput = try await Shell.readStdout(
+    "swift build --package-path \(testPackageDir) --experimental-swift-sdk \(bundleName)"
+  )
+  XCTAssertTrue(buildOutput.contains("Build complete!"))
+  logger.info("Test project built successfully")
+
+  try await Shell.run("rm -rf \(testPackageDir.appending(".build"))")
+
+  logger.info("Building test project with static-swift-stdlib")
+  buildOutput = try await Shell.readStdout(
+    "swift build --package-path \(testPackageDir) --experimental-swift-sdk \(bundleName) --static-swift-stdlib"
+  )
+  XCTAssertTrue(buildOutput.contains("Build complete!"))
+  logger.info("Test project built successfully")
+}
+
+func buildTestcases(config: SDKConfiguration) async throws {
+  var logger = Logger(label: "EndToEndTests")
+  logger[metadataKey: "testcase"] = "testPackageInitExecutable"
+
+  if ProcessInfo.processInfo.environment.keys.contains("JENKINS_URL") {
+    throw XCTSkip("EndToEnd tests cannot currently run in CI: https://github.com/swiftlang/swift-sdk-generator/issues/145")
+  }
+
+  if config.withDocker {
     do {
       try await Shell.run("docker ps")
-      possibleArguments.append("--with-docker --linux-distribution-name rhel --linux-distribution-version ubi9")
     } catch {
-      self.logger.warning("Docker CLI does not seem to be working, skipping tests that involve Docker.")
+      throw XCTSkip("Container runtime is not available - skipping tests which require it")
     }
+  }
 
-    for runArguments in possibleArguments {
-      if runArguments.contains("rhel") {
-        // Temporarily skip the RHEL-based SDK.  XCTSkip() is not suitable as it would skipping the entire test case
-        logger.warning("RHEL-based SDKs currently do not work with Swift 6.0: https://github.com/swiftlang/swift-sdk-generator/issues/138")
-        continue
-      }
+  let bundleName = try await FileManager.default.withTemporaryDirectory(logger: logger) { tempDir in
+    try await buildSDK(logger, scratchPath: tempDir.path, withArguments: config.sdkGeneratorArguments)
+  }
 
-      try await FileManager.default.withTemporaryDirectory(logger: logger) { tempDir in
-        let _ = try await buildSDK(inDirectory: packageDirectory, scratchPath: tempDir.path, withArguments: runArguments)
-        let _ = try await buildSDK(inDirectory: packageDirectory, scratchPath: tempDir.path, withArguments: runArguments)
-      }
+  logger.info("Built SDK")
+
+  for testcase in testcases {
+    try await FileManager.default.withTemporaryDirectory(logger: logger) { tempDir in
+      try await buildTestcase(logger, testcase: testcase, bundleName: bundleName, tempDir: tempDir)
     }
   }
 }
+
+final class Swift59_UbuntuEndToEndTests: XCTestCase {
+  let config = SDKConfiguration(
+    swiftVersion: "5.9.2",
+    linuxDistributionName: "ubuntu",
+    architecture: "aarch64",
+    withDocker: false
+  )
+
+  func testAarch64Direct() async throws {
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64"))
+  }
+
+  func testX86_64Direct() async throws {
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64"))
+  }
+
+  func testAarch64FromContainer() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/147")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64").withDocker())
+  }
+
+  func testX86_64FromContainer() async throws {
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64").withDocker())
+  }
+}
+
+final class Swift510_UbuntuEndToEndTests: XCTestCase {
+  let config = SDKConfiguration(
+    swiftVersion: "5.10.1",
+    linuxDistributionName: "ubuntu",
+    architecture: "aarch64",
+    withDocker: false
+  )
+
+  func testAarch64Direct() async throws {
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64"))
+  }
+
+  func testX86_64Direct() async throws {
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64"))
+  }
+
+  func testAarch64FromContainer() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/147")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64").withDocker())
+  }
+
+  func testX86_64FromContainer() async throws {
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64").withDocker())
+  }
+}
+
+final class Swift60_UbuntuEndToEndTests: XCTestCase {
+  let config = SDKConfiguration(
+    swiftVersion: "6.0.2",
+    linuxDistributionName: "ubuntu",
+    architecture: "aarch64",
+    withDocker: false
+  )
+
+  func testAarch64Direct() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/152")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64"))
+  }
+
+  func testX86_64Direct() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/152")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64"))
+  }
+
+  func testAarch64FromContainer() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/152")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64").withDocker())
+  }
+
+  func testX86_64FromContainer() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/152")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64").withDocker())
+  }
+}
+
+final class Swift59_RHELEndToEndTests: XCTestCase {
+  let config = SDKConfiguration(
+    swiftVersion: "5.9.2",
+    linuxDistributionName: "rhel",
+    architecture: "aarch64",
+    withDocker: true  // RHEL-based SDKs can only be built from containers
+  )
+
+  func testAarch64FromContainer() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/147")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64").withDocker())
+  }
+
+  func testX86_64FromContainer() async throws {
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64").withDocker())
+  }
+}
+
+final class Swift510_RHELEndToEndTests: XCTestCase {
+  let config = SDKConfiguration(
+    swiftVersion: "5.10.1",
+    linuxDistributionName: "rhel",
+    architecture: "aarch64",
+    withDocker: true  // RHEL-based SDKs can only be built from containers
+  )
+
+  func testAarch64FromContainer() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/147")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64").withDocker())
+  }
+
+  func testX86_64FromContainer() async throws {
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64").withDocker())
+  }
+}
+
+final class Swift60_RHELEndToEndTests: XCTestCase {
+  let config = SDKConfiguration(
+    swiftVersion: "6.0.2",
+    linuxDistributionName: "rhel",
+    architecture: "aarch64",
+    withDocker: true  // RHEL-based SDKs can only be built from containers
+  )
+
+  func testAarch64FromContainer() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/147")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("aarch64").withDocker())
+  }
+
+  func testX86_64FromContainer() async throws {
+    try skipBroken("https://github.com/swiftlang/swift-sdk-generator/issues/152")
+    try skipSlow()
+    try await buildTestcases(config: config.withArchitecture("x86_64").withDocker())
+  }
+}