diff --git a/documentation/project-docs/telemetry.md b/documentation/project-docs/telemetry.md
index e559f60bb25b..6db82f712ee1 100644
--- a/documentation/project-docs/telemetry.md
+++ b/documentation/project-docs/telemetry.md
@@ -61,7 +61,7 @@ Every telemetry event automatically includes these common properties:
 | **Telemetry Profile** | Custom telemetry profile (if set via env var) | Custom value or null |
 | **Docker Container** | Whether running in Docker container | `True` or `False` |
 | **CI** | Whether running in CI environment | `True` or `False` |
-| **LLM** | Detected LLM/assistant environment identifiers (comma-separated) | `claude`, `cursor`, `gemini`, `copilot`, `generic_agent` |
+| **LLM** | Detected LLM/assistant environment identifiers (comma-separated) | `claude`, `cursor`, `gemini`, `copilot`, `codex`, `aider`, `amp`, `qwen`, `droid`, `opencode`, `zed`, `kimi`, `openhands`, `goose`, `cline`, `roo`, `windsurf`, `generic_agent` |
 | **Current Path Hash** | SHA256 hash of current directory path | Hashed value |
 | **Machine ID** | SHA256 hash of machine MAC address (or GUID if unavailable) | Hashed value |
 | **Machine ID Old** | Legacy machine ID for compatibility | Hashed value |
diff --git a/src/Cli/Microsoft.DotNet.Cli.Definitions/Telemetry/EnvironmentDetectionRule.cs b/src/Cli/Microsoft.DotNet.Cli.Definitions/Telemetry/EnvironmentDetectionRule.cs
index 80d710d66cc0..ad9322a22633 100644
--- a/src/Cli/Microsoft.DotNet.Cli.Definitions/Telemetry/EnvironmentDetectionRule.cs
+++ b/src/Cli/Microsoft.DotNet.Cli.Definitions/Telemetry/EnvironmentDetectionRule.cs
@@ -69,6 +69,27 @@ public override bool IsMatch()
     }
 }
 
+/// <summary>
+/// Rule that matches when an environment variable contains a specific value (case-insensitive).
+/// </summary>
+internal class EnvironmentVariableValueRule : EnvironmentDetectionRule
+{
+    private readonly string _variable;
+    private readonly string _expectedValue;
+
+    public EnvironmentVariableValueRule(string variable, string expectedValue)
+    {
+        _variable = variable ?? throw new ArgumentNullException(nameof(variable));
+        _expectedValue = expectedValue ?? throw new ArgumentNullException(nameof(expectedValue));
+    }
+
+    public override bool IsMatch()
+    {
+        var value = Environment.GetEnvironmentVariable(_variable);
+        return !string.IsNullOrEmpty(value) && value.Equals(_expectedValue, StringComparison.OrdinalIgnoreCase);
+    }
+}
+
 /// <summary>
 /// Rule that matches when any of the specified environment variables is present and not null/empty,
 /// and returns the associated result value.
diff --git a/src/Cli/dotnet/Telemetry/LLMEnvironmentDetectorForTelemetry.cs b/src/Cli/dotnet/Telemetry/LLMEnvironmentDetectorForTelemetry.cs
index b37f9b5d0830..65368c4eef69 100644
--- a/src/Cli/dotnet/Telemetry/LLMEnvironmentDetectorForTelemetry.cs
+++ b/src/Cli/dotnet/Telemetry/LLMEnvironmentDetectorForTelemetry.cs
@@ -7,13 +7,39 @@ internal class LLMEnvironmentDetectorForTelemetry : ILLMEnvironmentDetector
 {
     private static readonly EnvironmentDetectionRuleWithResult<string>[] _detectionRules = [
         // Claude Code
-        new EnvironmentDetectionRuleWithResult<string>("claude", new AnyPresentEnvironmentRule("CLAUDECODE")),
+        new EnvironmentDetectionRuleWithResult<string>("claude", new AnyPresentEnvironmentRule("CLAUDECODE", "CLAUDE_CODE_ENTRYPOINT")),
         // Cursor AI
-        new EnvironmentDetectionRuleWithResult<string>("cursor", new AnyPresentEnvironmentRule("CURSOR_EDITOR")),
+        new EnvironmentDetectionRuleWithResult<string>("cursor", new AnyPresentEnvironmentRule("CURSOR_EDITOR", "CURSOR_AI")),
         // Gemini
         new EnvironmentDetectionRuleWithResult<string>("gemini", new BooleanEnvironmentRule("GEMINI_CLI")),
         // GitHub Copilot
         new EnvironmentDetectionRuleWithResult<string>("copilot", new BooleanEnvironmentRule("GITHUB_COPILOT_CLI_MODE")),
+        // Codex CLI
+        new EnvironmentDetectionRuleWithResult<string>("codex", new AnyPresentEnvironmentRule("CODEX_CLI", "CODEX_SANDBOX")),
+        // Aider
+        new EnvironmentDetectionRuleWithResult<string>("aider", new EnvironmentVariableValueRule("OR_APP_NAME", "Aider")),
+        // Amp
+        new EnvironmentDetectionRuleWithResult<string>("amp", new AnyPresentEnvironmentRule("AMP_HOME")),
+        // Qwen Code
+        new EnvironmentDetectionRuleWithResult<string>("qwen", new AnyPresentEnvironmentRule("QWEN_CODE")),
+        // Droid
+        new EnvironmentDetectionRuleWithResult<string>("droid", new BooleanEnvironmentRule("DROID_CLI")),
+        // OpenCode
+        new EnvironmentDetectionRuleWithResult<string>("opencode", new AnyPresentEnvironmentRule("OPENCODE_AI")),
+        // Zed AI
+        new EnvironmentDetectionRuleWithResult<string>("zed", new AnyPresentEnvironmentRule("ZED_ENVIRONMENT", "ZED_TERM")),
+        // Kimi CLI
+        new EnvironmentDetectionRuleWithResult<string>("kimi", new BooleanEnvironmentRule("KIMI_CLI")),
+        // OpenHands
+        new EnvironmentDetectionRuleWithResult<string>("openhands", new EnvironmentVariableValueRule("OR_APP_NAME", "OpenHands")),
+        // Goose
+        new EnvironmentDetectionRuleWithResult<string>("goose", new AnyPresentEnvironmentRule("GOOSE_TERMINAL")),
+        // Cline
+        new EnvironmentDetectionRuleWithResult<string>("cline", new AnyPresentEnvironmentRule("CLINE_TASK_ID")),
+        // Roo Code
+        new EnvironmentDetectionRuleWithResult<string>("roo", new AnyPresentEnvironmentRule("ROO_CODE_TASK_ID")),
+        // Windsurf
+        new EnvironmentDetectionRuleWithResult<string>("windsurf", new AnyPresentEnvironmentRule("WINDSURF_SESSION")),
         // (proposed) generic flag for Agentic usage
         new EnvironmentDetectionRuleWithResult<string>("generic_agent", new BooleanEnvironmentRule("AGENT_CLI")),
     ];
diff --git a/test/dotnet.Tests/TelemetryCommonPropertiesTests.cs b/test/dotnet.Tests/TelemetryCommonPropertiesTests.cs
index 4e28b92479d7..188faf237128 100644
--- a/test/dotnet.Tests/TelemetryCommonPropertiesTests.cs
+++ b/test/dotnet.Tests/TelemetryCommonPropertiesTests.cs
@@ -231,17 +231,44 @@ public void TelemetryCommonPropertiesShouldContainSessionId(string? sessionId)
         public static TheoryData<Dictionary<string, string>?, string?> LLMTelemetryTestCases => new()
         {
             { new Dictionary<string, string> { {"CLAUDECODE", "1" } }, "claude" },
+            { new Dictionary<string, string> { {"CLAUDE_CODE_ENTRYPOINT", "some_value" } }, "claude" },
             { new Dictionary<string, string> { { "CURSOR_EDITOR", "1" } }, "cursor" },
+            { new Dictionary<string, string> { { "CURSOR_AI", "1" } }, "cursor" },
             { new Dictionary<string, string> { { "GEMINI_CLI", "true" } }, "gemini" },
             { new Dictionary<string, string> { { "GITHUB_COPILOT_CLI_MODE", "true" } }, "copilot" },
+            { new Dictionary<string, string> { { "CODEX_CLI", "1" } }, "codex" },
+            { new Dictionary<string, string> { { "CODEX_SANDBOX", "1" } }, "codex" },
+            { new Dictionary<string, string> { { "OR_APP_NAME", "Aider" } }, "aider" },
+            { new Dictionary<string, string> { { "OR_APP_NAME", "aider" } }, "aider" },
+            { new Dictionary<string, string> { { "AMP_HOME", "/path/to/amp" } }, "amp" },
+            { new Dictionary<string, string> { { "QWEN_CODE", "1" } }, "qwen" },
+            { new Dictionary<string, string> { { "DROID_CLI", "true" } }, "droid" },
+            { new Dictionary<string, string> { { "OPENCODE_AI", "1" } }, "opencode" },
+            { new Dictionary<string, string> { { "ZED_ENVIRONMENT", "1" } }, "zed" },
+            { new Dictionary<string, string> { { "ZED_TERM", "1" } }, "zed" },
+            { new Dictionary<string, string> { { "KIMI_CLI", "true" } }, "kimi" },
+            { new Dictionary<string, string> { { "OR_APP_NAME", "OpenHands" } }, "openhands" },
+            { new Dictionary<string, string> { { "OR_APP_NAME", "openhands" } }, "openhands" },
+            { new Dictionary<string, string> { { "GOOSE_TERMINAL", "1" } }, "goose" },
+            { new Dictionary<string, string> { { "CLINE_TASK_ID", "task123" } }, "cline" },
+            { new Dictionary<string, string> { { "ROO_CODE_TASK_ID", "task456" } }, "roo" },
+            { new Dictionary<string, string> { { "WINDSURF_SESSION", "session789" } }, "windsurf" },
             { new Dictionary<string, string> { { "AGENT_CLI", "true" } }, "generic_agent" },
+            // Test combinations of older tools
             { new Dictionary<string, string> { { "CLAUDECODE", "1" }, { "CURSOR_EDITOR", "1" } }, "claude, cursor" },
             { new Dictionary<string, string> { { "GEMINI_CLI", "true" }, { "GITHUB_COPILOT_CLI_MODE", "true" } }, "gemini, copilot" },
             { new Dictionary<string, string> { { "CLAUDECODE", "1" }, { "GEMINI_CLI", "true" }, { "AGENT_CLI", "true" } }, "claude, gemini, generic_agent" },
             { new Dictionary<string, string> { { "CLAUDECODE", "1" }, { "CURSOR_EDITOR", "1" }, { "GEMINI_CLI", "true" }, { "GITHUB_COPILOT_CLI_MODE", "true" }, { "AGENT_CLI", "true" } }, "claude, cursor, gemini, copilot, generic_agent" },
+            // Test combinations of newer tools
+            { new Dictionary<string, string> { { "OR_APP_NAME", "Aider" }, { "CLINE_TASK_ID", "task123" } }, "aider, cline" },
+            { new Dictionary<string, string> { { "CODEX_CLI", "1" }, { "WINDSURF_SESSION", "session789" } }, "codex, windsurf" },
+            { new Dictionary<string, string> { { "GOOSE_TERMINAL", "1" }, { "ROO_CODE_TASK_ID", "task456" } }, "goose, roo" },
             { new Dictionary<string, string> { { "GEMINI_CLI", "false" } }, null },
             { new Dictionary<string, string> { { "GITHUB_COPILOT_CLI_MODE", "false" } }, null },
             { new Dictionary<string, string> { { "AGENT_CLI", "false" } }, null },
+            { new Dictionary<string, string> { { "DROID_CLI", "false" } }, null },
+            { new Dictionary<string, string> { { "KIMI_CLI", "false" } }, null },
+            { new Dictionary<string, string> { { "OR_APP_NAME", "SomeOtherApp" } }, null },
             { new Dictionary<string, string>(), null },
         };