diff --git a/cmd/analytics/analytics.go b/cmd/analytics/analytics.go
index 62d4a0e51..b4dd48eda 100644
--- a/cmd/analytics/analytics.go
+++ b/cmd/analytics/analytics.go
@@ -4,6 +4,7 @@ import (
 	_ "embed"
 	"encoding/json"
 	"os"
+	"strings"
 
 	"github.com/launchdarkly/ldcli/cmd/cliflags"
 
@@ -30,19 +31,48 @@ func (osEnvChecker) StdoutFd() int            { return int(os.Stdout.Fd()) }
 //go:embed known_agents.json
 var knownAgentsJSON []byte
 
+// agentEnvVar maps an environment variable to an agent label. If Equals or
+// Contains is set, the value must also match. Otherwise any non-empty value
+// matches.
+// agentEnvVar maps an environment variable to an agent label. If Equals or
+// Contains is set, the value must also match. Otherwise any non-empty value
+// matches.
 type agentEnvVar struct {
-	EnvVar string `json:"env_var"`
+	EnvVar   string `json:"env_var"`
+	Equals   string `json:"equals,omitempty"`
+	Contains string `json:"contains,omitempty"`
+	Label    string `json:"label"`
+}
+
+func (a agentEnvVar) matches(value string) bool {
+	switch {
+	case value == "":
+		return false
+	case a.Equals != "":
+		return value == a.Equals
+	case a.Contains != "":
+		return strings.Contains(value, a.Contains)
+	default:
+		return true
+	}
+}
+
+// aiAgentPrefix maps the start of an AI_AGENT value to an agent label.
+type aiAgentPrefix struct {
+	Prefix string `json:"prefix"`
 	Label  string `json:"label"`
 }
 
 type knownAgentsConfig struct {
-	Agents    []agentEnvVar `json:"agents"`
-	CIEnvVars []string      `json:"ci_env_vars"`
+	AIAgentPrefixes []aiAgentPrefix `json:"ai_agent_prefixes"`
+	Agents          []agentEnvVar   `json:"agents"`
+	CIEnvVars       []string        `json:"ci_env_vars"`
 }
 
 var (
-	knownAgentEnvVars []agentEnvVar
-	knownCIEnvVars    []string
+	knownAIAgentPrefixes []aiAgentPrefix
+	knownAgentEnvVars    []agentEnvVar
+	knownCIEnvVars       []string
 )
 
 func init() {
@@ -50,6 +80,7 @@ func init() {
 	if err := json.Unmarshal(knownAgentsJSON, &cfg); err != nil {
 		panic("failed to parse embedded known_agents.json: " + err.Error())
 	}
+	knownAIAgentPrefixes = cfg.AIAgentPrefixes
 	knownAgentEnvVars = cfg.Agents
 	knownCIEnvVars = cfg.CIEnvVars
 }
@@ -65,8 +96,12 @@ func detectAgentContext(env envChecker) string {
 		return "explicit:" + v
 	}
 
+	if label := aiAgentLabel(env.Getenv("AI_AGENT")); label != "" {
+		return label
+	}
+
 	for _, a := range knownAgentEnvVars {
-		if env.Getenv(a.EnvVar) != "" {
+		if a.matches(env.Getenv(a.EnvVar)) {
 			return a.Label
 		}
 	}
@@ -84,6 +119,61 @@ func detectAgentContext(env envChecker) string {
 	return "unknown-non-interactive"
 }
 
+// maxAIAgentNameLen limits the length of an unknown AI_AGENT name in a label.
+const maxAIAgentNameLen = 32
+
+// aiAgentLabel converts an AI_AGENT value to a label. AI_AGENT is a shared
+// convention: the value starts with the agent name and can have a version
+// after it, for example "claude-code_2-1-295_agent" or "devin@1". A known
+// name gets its label. An unknown name gets "ai-agent:<name>", without the
+// version. The function returns "" if the value has no usable name.
+func aiAgentLabel(value string) string {
+	value = strings.ToLower(strings.TrimSpace(value))
+	if value == "" {
+		return ""
+	}
+
+	for _, p := range knownAIAgentPrefixes {
+		if hasNamePrefix(value, p.Prefix) {
+			return p.Label
+		}
+	}
+
+	name, _, _ := strings.Cut(value, "@")
+	name, _, _ = strings.Cut(name, "_")
+	name = strings.Map(func(r rune) rune {
+		if (r >= 'a' && r <= 'z') || (r >= '0' && r <= '9') || r == '-' {
+			return r
+		}
+		return -1
+	}, name)
+	if len(name) > maxAIAgentNameLen {
+		name = name[:maxAIAgentNameLen]
+	}
+	if name == "" {
+		return ""
+	}
+
+	return "ai-agent:" + name
+}
+
+// hasNamePrefix reports whether value starts with prefix and the prefix ends at
+// a name boundary. For example, "amp" matches "amp" and "amp_1" but not "ampere".
+func hasNamePrefix(value, prefix string) bool {
+	if !strings.HasPrefix(value, prefix) {
+		return false
+	}
+	if len(value) == len(prefix) {
+		return true
+	}
+	switch value[len(prefix)] {
+	case '_', '@', '-':
+		return true
+	default:
+		return false
+	}
+}
+
 func CmdRunEventProperties(
 	cmd *cobra.Command,
 	name string,
diff --git a/cmd/analytics/analytics_test.go b/cmd/analytics/analytics_test.go
index 34d6fd337..969390174 100644
--- a/cmd/analytics/analytics_test.go
+++ b/cmd/analytics/analytics_test.go
@@ -1,6 +1,7 @@
 package analytics
 
 import (
+	"strings"
 	"testing"
 
 	"github.com/spf13/cobra"
@@ -39,65 +40,236 @@ func TestDetectAgentContext(t *testing.T) {
 			expected: "explicit:my-skill",
 		},
 		{
-			name:     "explicit LD_CLI_AGENT takes precedence over known env vars",
-			env:      newMockEnv(map[string]string{"LD_CLI_AGENT": "custom", "CURSOR_SESSION_ID": "abc"}, false),
+			name:     "explicit LD_CLI_AGENT takes precedence over AI_AGENT and known env vars",
+			env:      newMockEnv(map[string]string{"LD_CLI_AGENT": "custom", "AI_AGENT": "devin_1_agent", "CLAUDECODE": "1"}, false),
 			expected: "explicit:custom",
 		},
+
+		// Environment variables that each agent sets in the shell that runs ldcli.
+		{
+			name: "Claude Code",
+			env: newMockEnv(map[string]string{
+				"AI_AGENT":               "claude-code_2-1-295_agent",
+				"CLAUDECODE":             "1",
+				"CLAUDE_CODE_ENTRYPOINT": "cli",
+				"CLAUDE_CODE_SESSION_ID": "1366a0bd-a5d9-4aef-a2b1-e96a3a313a34",
+			}, false),
+			expected: "claude-code",
+		},
+		{
+			name:     "Claude Code before AI_AGENT support",
+			env:      newMockEnv(map[string]string{"CLAUDECODE": "1", "CLAUDE_CODE_ENTRYPOINT": "cli"}, false),
+			expected: "claude-code",
+		},
 		{
-			name:     "CURSOR_SESSION_ID detected",
-			env:      newMockEnv(map[string]string{"CURSOR_SESSION_ID": "abc"}, false),
+			name:     "Cursor agent",
+			env:      newMockEnv(map[string]string{"CURSOR_AGENT": "1"}, false),
 			expected: "cursor",
 		},
 		{
-			name:     "CURSOR_TRACE_ID detected",
-			env:      newMockEnv(map[string]string{"CURSOR_TRACE_ID": "xyz"}, false),
+			name:     "Cursor agent terminal role",
+			env:      newMockEnv(map[string]string{"CURSOR_EXTENSION_HOST_ROLE": "agent-exec"}, false),
 			expected: "cursor",
 		},
 		{
-			name:     "CLAUDE_CODE detected",
-			env:      newMockEnv(map[string]string{"CLAUDE_CODE": "1"}, false),
-			expected: "claude-code",
+			name:     "Cursor builds that also set CI=1",
+			env:      newMockEnv(map[string]string{"CURSOR_AGENT": "1", "CI": "1"}, false),
+			expected: "cursor",
 		},
 		{
-			name:     "CLAUDE_CODE_SESSION detected",
-			env:      newMockEnv(map[string]string{"CLAUDE_CODE_SESSION": "sess"}, false),
-			expected: "claude-code",
+			name: "Codex CLI",
+			env: newMockEnv(map[string]string{
+				"CODEX_THREAD_ID":                "t-1",
+				"CODEX_SESSION_ID":               "s-1",
+				"CODEX_SANDBOX_NETWORK_DISABLED": "1",
+			}, false),
+			expected: "codex",
 		},
 		{
-			name:     "CODEX_SESSION detected",
-			env:      newMockEnv(map[string]string{"CODEX_SESSION": "s"}, false),
+			name:     "Codex CLI unified exec",
+			env:      newMockEnv(map[string]string{"CODEX_CI": "1"}, false),
 			expected: "codex",
 		},
 		{
-			name:     "CODEX_SANDBOX_ID detected",
-			env:      newMockEnv(map[string]string{"CODEX_SANDBOX_ID": "sb"}, false),
+			name:     "Codex CLI macOS sandbox",
+			env:      newMockEnv(map[string]string{"CODEX_SANDBOX": "seatbelt"}, false),
 			expected: "codex",
 		},
 		{
-			name:     "DEVIN_SESSION detected",
-			env:      newMockEnv(map[string]string{"DEVIN_SESSION": "d"}, false),
+			name:     "Devin",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "devin_3000-11-1_agent"}, false),
 			expected: "devin",
 		},
 		{
-			name:     "GITHUB_COPILOT detected",
-			env:      newMockEnv(map[string]string{"GITHUB_COPILOT": "1"}, false),
+			name: "GitHub Copilot in VS Code",
+			env: newMockEnv(map[string]string{
+				"AI_AGENT":      "github_copilot_vscode_agent",
+				"COPILOT_AGENT": "1",
+				"TERM_PROGRAM":  "vscode",
+			}, true),
 			expected: "copilot",
 		},
 		{
-			name:     "WINDSURF_SESSION detected",
-			env:      newMockEnv(map[string]string{"WINDSURF_SESSION": "w"}, false),
-			expected: "windsurf",
+			name:     "GitHub Copilot CLI",
+			env:      newMockEnv(map[string]string{"COPILOT_CLI": "1", "COPILOT_AGENT_SESSION_ID": "s-1"}, false),
+			expected: "copilot",
+		},
+		{
+			name:     "Gemini CLI",
+			env:      newMockEnv(map[string]string{"GEMINI_CLI": "1"}, false),
+			expected: "gemini-cli",
+		},
+		{
+			name:     "OpenCode",
+			env:      newMockEnv(map[string]string{"OPENCODE": "1", "AGENT": "1", "OPENCODE_PID": "42"}, false),
+			expected: "opencode",
+		},
+		{
+			name:     "Kilo Code also sets OPENCODE",
+			env:      newMockEnv(map[string]string{"KILO": "1", "KILOCODE_FEATURE": "cli", "OPENCODE": "1", "AGENT": "1"}, false),
+			expected: "kilo-code",
+		},
+		{
+			name:     "Crush",
+			env:      newMockEnv(map[string]string{"CRUSH": "1", "AGENT": "crush", "AI_AGENT": "crush"}, false),
+			expected: "crush",
+		},
+		{
+			name:     "Augment",
+			env:      newMockEnv(map[string]string{"AUGMENT_AGENT": "1"}, false),
+			expected: "augment",
 		},
 		{
-			name:     "CLINE_TASK_ID detected",
-			env:      newMockEnv(map[string]string{"CLINE_TASK_ID": "t"}, false),
+			name:     "Cline in a VS Code terminal",
+			env:      newMockEnv(map[string]string{"CLINE_ACTIVE": "true", "TERM_PROGRAM": "vscode"}, true),
 			expected: "cline",
 		},
 		{
-			name:     "AIDER_MODEL detected",
-			env:      newMockEnv(map[string]string{"AIDER_MODEL": "gpt-4"}, false),
+			name:     "Roo Code in a VS Code terminal",
+			env:      newMockEnv(map[string]string{"ROO_ACTIVE": "true"}, true),
+			expected: "roo-code",
+		},
+		{
+			name:     "Roo Code CLI",
+			env:      newMockEnv(map[string]string{"ROO_CLI_RUNTIME": "1"}, false),
+			expected: "roo-code",
+		},
+		{
+			name:     "Amp",
+			env:      newMockEnv(map[string]string{"AMP_CURRENT_THREAD_ID": "T-1"}, false),
+			expected: "amp",
+		},
+		{
+			name:     "Windsurf Cascade",
+			env:      newMockEnv(map[string]string{"WINDSURF_CASCADE_TERMINAL": "1"}, false),
+			expected: "windsurf",
+		},
+		{
+			name:     "Amazon Q Developer CLI",
+			env:      newMockEnv(map[string]string{"AWS_EXECUTION_ENV": "AmazonQ-For-CLI Version/1.12.0"}, false),
+			expected: "amazon-q",
+		},
+		{
+			name:     "Aider",
+			env:      newMockEnv(map[string]string{"OR_APP_NAME": "Aider", "OR_SITE_URL": "https://aider.chat"}, false),
 			expected: "aider",
 		},
+
+		// AI_AGENT parsing.
+		{
+			name:     "AI_AGENT takes precedence over agent env vars",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "claude-code_2-1-295_agent", "CODEX_THREAD_ID": "t-1"}, false),
+			expected: "claude-code",
+		},
+		{
+			name:     "AI_AGENT with an @ version",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "devin@1"}, false),
+			expected: "devin",
+		},
+		{
+			name:     "AI_AGENT is not case sensitive",
+			env:      newMockEnv(map[string]string{"AI_AGENT": " Claude-Code_2-1-295_agent "}, false),
+			expected: "claude-code",
+		},
+		{
+			name:     "AI_AGENT with an unknown name drops the version",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "hermes-agent_0-4_agent"}, false),
+			expected: "ai-agent:hermes-agent",
+		},
+		{
+			name:     "AI_AGENT prefix must end at a name boundary",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "ampere"}, false),
+			expected: "ai-agent:ampere",
+		},
+		{
+			name:     "AI_AGENT removes characters that are not allowed",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "my agent!/../x"}, false),
+			expected: "ai-agent:myagentx",
+		},
+		{
+			name:     "AI_AGENT with a long unknown name is cut",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "abcdefghijklmnopqrstuvwxyz0123456789"}, false),
+			expected: "ai-agent:abcdefghijklmnopqrstuvwxyz012345",
+		},
+		{
+			name:     "AI_AGENT with no usable name is ignored",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "_@!!"}, false),
+			expected: "unknown-non-interactive",
+		},
+		{
+			name:     "AI_AGENT that is only spaces is ignored",
+			env:      newMockEnv(map[string]string{"AI_AGENT": "   "}, true),
+			expected: "",
+		},
+
+		// Values that must not match.
+		{
+			name:     "AWS_EXECUTION_ENV without AmazonQ is not an agent",
+			env:      newMockEnv(map[string]string{"AWS_EXECUTION_ENV": "AWS_Lambda_go1.x"}, false),
+			expected: "unknown-non-interactive",
+		},
+		{
+			name:     "OR_APP_NAME for another app is not an agent",
+			env:      newMockEnv(map[string]string{"OR_APP_NAME": "SomeOtherApp"}, false),
+			expected: "unknown-non-interactive",
+		},
+		{
+			name:     "CURSOR_EXTENSION_HOST_ROLE for a person is not an agent",
+			env:      newMockEnv(map[string]string{"CURSOR_EXTENSION_HOST_ROLE": "user"}, true),
+			expected: "",
+		},
+		{
+			name:     "person in the Cursor terminal is not an agent",
+			env:      newMockEnv(map[string]string{"CURSOR_TRACE_ID": "xyz", "TERM_PROGRAM": "vscode"}, true),
+			expected: "",
+		},
+		{
+			name:     "person with AIDER_MODEL in the shell profile is not an agent",
+			env:      newMockEnv(map[string]string{"AIDER_MODEL": "gpt-4"}, true),
+			expected: "",
+		},
+		{
+			name:     "Replit workspace is not an agent",
+			env:      newMockEnv(map[string]string{"REPL_ID": "r-1"}, true),
+			expected: "",
+		},
+		{
+			name: "environment variables that no agent sets are not detected",
+			env: newMockEnv(map[string]string{
+				"CLAUDE_CODE":         "1",
+				"CLAUDE_CODE_SESSION": "s",
+				"CURSOR_SESSION_ID":   "c",
+				"CODEX_SESSION":       "s",
+				"CODEX_SANDBOX_ID":    "sb",
+				"DEVIN_SESSION":       "d",
+				"GITHUB_COPILOT":      "1",
+				"WINDSURF_SESSION":    "w",
+				"CLINE_TASK_ID":       "t",
+			}, false),
+			expected: "unknown-non-interactive",
+		},
+
+		// Terminal and CI fallbacks.
 		{
 			name:     "no TTY and no env vars returns unknown-non-interactive",
 			env:      newMockEnv(map[string]string{}, false),
@@ -120,8 +292,8 @@ func TestDetectAgentContext(t *testing.T) {
 		},
 		{
 			name:     "agent env var takes precedence over CI env var",
-			env:      newMockEnv(map[string]string{"CURSOR_SESSION_ID": "abc", "CI": "true"}, false),
-			expected: "cursor",
+			env:      newMockEnv(map[string]string{"COPILOT_AGENT": "1", "GITHUB_ACTIONS": "true", "CI": "true"}, false),
+			expected: "copilot",
 		},
 		{
 			name:     "interactive terminal with no agent env vars returns empty",
@@ -133,11 +305,6 @@ func TestDetectAgentContext(t *testing.T) {
 			env:      newMockEnv(map[string]string{"CI": "true"}, true),
 			expected: "",
 		},
-		{
-			name:     "first matching env var wins by priority order",
-			env:      newMockEnv(map[string]string{"CURSOR_SESSION_ID": "c", "CLAUDE_CODE": "1"}, false),
-			expected: "cursor",
-		},
 		{
 			name:     "stdin is TTY but stdout is not still counts as interactive",
 			env:      mockEnvChecker{envVars: map[string]string{}, stdinTerminal: true, stdoutTerminal: false},
@@ -158,6 +325,23 @@ func TestDetectAgentContext(t *testing.T) {
 	}
 }
 
+func TestKnownAgentsConfig(t *testing.T) {
+	assert.NotEmpty(t, knownAIAgentPrefixes)
+	assert.NotEmpty(t, knownAgentEnvVars)
+	assert.NotEmpty(t, knownCIEnvVars)
+
+	for _, p := range knownAIAgentPrefixes {
+		assert.NotEmpty(t, p.Prefix)
+		assert.NotEmpty(t, p.Label, "prefix %q", p.Prefix)
+		assert.Equal(t, strings.ToLower(p.Prefix), p.Prefix, "prefix %q must be lowercase", p.Prefix)
+	}
+	for _, a := range knownAgentEnvVars {
+		assert.NotEmpty(t, a.EnvVar)
+		assert.NotEmpty(t, a.Label, "env var %q", a.EnvVar)
+		assert.False(t, a.Equals != "" && a.Contains != "", "env var %q sets both equals and contains", a.EnvVar)
+	}
+}
+
 func TestCmdRunEventProperties(t *testing.T) {
 	t.Run("does not set agent_context itself", func(t *testing.T) {
 		cmd := &cobra.Command{Use: "test"}
diff --git a/cmd/analytics/known_agents.json b/cmd/analytics/known_agents.json
index 507296fcd..7dda6939a 100644
--- a/cmd/analytics/known_agents.json
+++ b/cmd/analytics/known_agents.json
@@ -1,16 +1,42 @@
 {
+  "ai_agent_prefixes": [
+    {"prefix": "claude-code", "label": "claude-code"},
+    {"prefix": "github_copilot", "label": "copilot"},
+    {"prefix": "github-copilot", "label": "copilot"},
+    {"prefix": "copilot", "label": "copilot"},
+    {"prefix": "cursor", "label": "cursor"},
+    {"prefix": "codex", "label": "codex"},
+    {"prefix": "devin", "label": "devin"},
+    {"prefix": "gemini", "label": "gemini-cli"},
+    {"prefix": "kilo", "label": "kilo-code"},
+    {"prefix": "opencode", "label": "opencode"},
+    {"prefix": "crush", "label": "crush"},
+    {"prefix": "amp", "label": "amp"},
+    {"prefix": "goose", "label": "goose"},
+    {"prefix": "openhands", "label": "openhands"}
+  ],
   "agents": [
-    {"env_var": "CURSOR_SESSION_ID", "label": "cursor"},
-    {"env_var": "CURSOR_TRACE_ID", "label": "cursor"},
-    {"env_var": "CLAUDE_CODE", "label": "claude-code"},
-    {"env_var": "CLAUDE_CODE_SESSION", "label": "claude-code"},
-    {"env_var": "CODEX_SESSION", "label": "codex"},
-    {"env_var": "CODEX_SANDBOX_ID", "label": "codex"},
-    {"env_var": "DEVIN_SESSION", "label": "devin"},
-    {"env_var": "GITHUB_COPILOT", "label": "copilot"},
-    {"env_var": "WINDSURF_SESSION", "label": "windsurf"},
-    {"env_var": "CLINE_TASK_ID", "label": "cline"},
-    {"env_var": "AIDER_MODEL", "label": "aider"}
+    {"env_var": "CLAUDECODE", "label": "claude-code"},
+    {"env_var": "CURSOR_AGENT", "label": "cursor"},
+    {"env_var": "CURSOR_EXTENSION_HOST_ROLE", "equals": "agent-exec", "label": "cursor"},
+    {"env_var": "CODEX_THREAD_ID", "label": "codex"},
+    {"env_var": "CODEX_SESSION_ID", "label": "codex"},
+    {"env_var": "CODEX_CI", "label": "codex"},
+    {"env_var": "CODEX_SANDBOX", "label": "codex"},
+    {"env_var": "GEMINI_CLI", "label": "gemini-cli"},
+    {"env_var": "KILO", "label": "kilo-code"},
+    {"env_var": "OPENCODE", "label": "opencode"},
+    {"env_var": "CRUSH", "label": "crush"},
+    {"env_var": "COPILOT_AGENT", "label": "copilot"},
+    {"env_var": "COPILOT_CLI", "label": "copilot"},
+    {"env_var": "AUGMENT_AGENT", "label": "augment"},
+    {"env_var": "CLINE_ACTIVE", "label": "cline"},
+    {"env_var": "ROO_ACTIVE", "label": "roo-code"},
+    {"env_var": "ROO_CLI_RUNTIME", "label": "roo-code"},
+    {"env_var": "AMP_CURRENT_THREAD_ID", "label": "amp"},
+    {"env_var": "WINDSURF_CASCADE_TERMINAL", "label": "windsurf"},
+    {"env_var": "AWS_EXECUTION_ENV", "contains": "AmazonQ", "label": "amazon-q"},
+    {"env_var": "OR_APP_NAME", "equals": "Aider", "label": "aider"}
   ],
   "ci_env_vars": [
     "CI",
diff --git a/cmd/root.go b/cmd/root.go
index dd9266bd3..e86795e2e 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -412,10 +412,6 @@ See each command's help for details on how to use the generated script.`, rootCm
 	case err != nil:
 		outcome = analytics.ERROR
 		fmt.Fprintln(os.Stderr, err.Error())
-		// Give the background check a moment to write the cache. os.Exit
-		// would otherwise kill it immediately.
-		waitForUpdateNotice()
-		os.Exit(1)
 	default:
 		outcome = analytics.SUCCESS
 	}
@@ -438,6 +434,12 @@ See each command's help for details on how to use the generated script.`, rootCm
 	analyticsClient.Wait()
 
 	waitForUpdateNotice()
+
+	// Exit after the completed event is sent. os.Exit stops the process
+	// immediately, so an earlier exit lost the error event.
+	if outcome == analytics.ERROR {
+		os.Exit(1)
+	}
 }
 
 // setFlagsFromConfig reads in the config file if it exists and uses any flag values for commands.