diff --git a/packages/cli/src/cli-program-telemetry.test.ts b/packages/cli/src/cli-program-telemetry.test.ts
index 63215f0b..936a0aa4 100644
--- a/packages/cli/src/cli-program-telemetry.test.ts
+++ b/packages/cli/src/cli-program-telemetry.test.ts
@@ -77,6 +77,8 @@ describe('runCommanderKtxCli telemetry', () => {
     expect(statusIo.stderr()).toContain('[telemetry]');
     expect(statusIo.stderr()).toContain('"event":"command"');
     expect(statusIo.stderr()).toContain('"commandPath":["ktx","status"]');
+    expect(statusIo.stderr()).toContain('"event":"project_stack_snapshot"');
+    expect(statusIo.stderr()).toContain('"connectionCount"');
     expect(statusIo.stderr()).not.toContain(tempDir);
   });
 
diff --git a/packages/cli/src/commands/status-commands.ts b/packages/cli/src/commands/status-commands.ts
index e2adf8f1..ec429576 100644
--- a/packages/cli/src/commands/status-commands.ts
+++ b/packages/cli/src/commands/status-commands.ts
@@ -2,6 +2,7 @@ import type { Command } from '@commander-js/extra-typings';
 import type { KtxCliCommandContext } from '../cli-program.js';
 import { resolveCommandProjectDir, resolveCommandProjectDirOverride } from '../cli-program.js';
 import { findNearestKtxProjectDir } from '../project-resolver.js';
+import { emitProjectStackSnapshot } from '../telemetry/index.js';
 
 function outputMode(options: { json?: boolean }): 'plain' | 'json' {
   return options.json === true ? 'json' : 'plain';
@@ -58,11 +59,12 @@ export function registerStatusCommands(program: Command, context: KtxCliCommandC
           );
           return;
         }
+        const projectDir = resolveCommandProjectDir(command);
         context.setExitCode(
           await runner(
             {
               command: 'project',
-              projectDir: resolveCommandProjectDir(command),
+              projectDir,
               outputMode: outputMode(options),
               verbose: options.verbose === true,
               fast: options.fast === true,
@@ -71,6 +73,11 @@ export function registerStatusCommands(program: Command, context: KtxCliCommandC
             context.io,
           ),
         );
+        await emitProjectStackSnapshot({
+          projectDir,
+          io: context.io,
+          packageInfo: context.packageInfo,
+        });
       },
     );
 }
diff --git a/packages/cli/src/connection.test.ts b/packages/cli/src/connection.test.ts
index b05a6f16..7cfc5b93 100644
--- a/packages/cli/src/connection.test.ts
+++ b/packages/cli/src/connection.test.ts
@@ -20,6 +20,7 @@ function makeIo() {
   return {
     io: {
       stdout: {
+        isTTY: true,
         write: (chunk: string) => {
           stdout += chunk;
         },
@@ -72,6 +73,7 @@ describe('runKtxConnection', () => {
   });
 
   afterEach(async () => {
+    vi.unstubAllEnvs();
     await rm(tempDir, { recursive: true, force: true });
   });
 
@@ -137,6 +139,27 @@ describe('runKtxConnection', () => {
     expect(io.stdout()).toContain('Status: ok');
   });
 
+  it('emits debug telemetry for connection tests without project paths', async () => {
+    vi.stubEnv('KTX_TELEMETRY_DEBUG', '1');
+    vi.stubEnv('CI', '');
+    const projectDir = join(tempDir, 'project');
+    await initKtxProject({ projectDir });
+    await writeConnections(projectDir, {
+      warehouse: { driver: 'postgres', url: 'env:DATABASE_URL' },
+    });
+    const { connector } = nativeConnector('postgres');
+    const io = makeIo();
+
+    const code = await runKtxConnection({ command: 'test', projectDir, connectionId: 'warehouse' }, io.io, {
+      createScanConnector: vi.fn(async () => connector),
+    });
+
+    expect(code).toBe(0);
+    expect(io.stderr()).toContain('"event":"connection_test"');
+    expect(io.stderr()).toContain('"driver":"postgres"');
+    expect(io.stderr()).not.toContain(projectDir);
+  });
+
   it('reports the connector error and still cleans up when native testConnection fails', async () => {
     const projectDir = join(tempDir, 'project');
     await initKtxProject({ projectDir });
diff --git a/packages/cli/src/connection.ts b/packages/cli/src/connection.ts
index 174fe5ad..bb99d4fd 100644
--- a/packages/cli/src/connection.ts
+++ b/packages/cli/src/connection.ts
@@ -14,6 +14,9 @@ import type { KtxCliIo } from './index.js';
 import { bold, dim, green, red, SYMBOLS } from './io/symbols.js';
 import { createKtxCliScanConnector } from './local-scan-connectors.js';
 import { profileMark } from './startup-profile.js';
+import { isDemoConnection } from './telemetry/demo-detect.js';
+import { emitTelemetryEvent } from './telemetry/index.js';
+import { scrubErrorClass } from './telemetry/scrubber.js';
 
 profileMark('module:connection');
 
@@ -300,6 +303,30 @@ interface ConnectionTestRow {
   detail: string;
 }
 
+async function emitConnectionTest(input: {
+  project: KtxLocalProject;
+  connectionId: string;
+  driver: string;
+  outcome: 'ok' | 'error';
+  durationMs: number;
+  error?: unknown;
+  io: KtxCliIo;
+}): Promise<void> {
+  const errorClass = input.error ? scrubErrorClass(input.error) : undefined;
+  await emitTelemetryEvent({
+    name: 'connection_test',
+    projectDir: input.project.projectDir,
+    io: input.io,
+    fields: {
+      driver: input.driver,
+      isDemoConnection: isDemoConnection(input.connectionId, input.project.config.connections[input.connectionId]),
+      outcome: input.outcome,
+      durationMs: input.durationMs,
+      ...(errorClass ? { errorClass } : {}),
+    },
+  });
+}
+
 function visualWidth(text: string): number {
   // styleText wraps content in ANSI escape sequences; strip them before measuring.
   return text.replace(/\[[0-9;]*m/g, '').length;
@@ -352,8 +379,17 @@ async function runTestAll(
   const rows = await Promise.all(
     entries.map(async ([connectionId, connection]): Promise<ConnectionTestRow> => {
       const declaredDriver = String(connection.driver ?? '').trim().toLowerCase() || 'unknown';
+      const startedAt = performance.now();
       try {
         const outcome = await testConnectionByDriver(project, connectionId, deps);
+        await emitConnectionTest({
+          project,
+          connectionId,
+          driver: outcome.driver || declaredDriver,
+          outcome: 'ok',
+          durationMs: Math.max(0, performance.now() - startedAt),
+          io,
+        });
         return {
           connectionId,
           driver: outcome.driver || declaredDriver,
@@ -361,6 +397,15 @@ async function runTestAll(
           detail: `${outcome.detailKey}: ${outcome.detailValue}`,
         };
       } catch (error) {
+        await emitConnectionTest({
+          project,
+          connectionId,
+          driver: declaredDriver,
+          outcome: 'error',
+          durationMs: Math.max(0, performance.now() - startedAt),
+          error,
+          io,
+        });
         return {
           connectionId,
           driver: declaredDriver,
@@ -403,7 +448,35 @@ export async function runKtxConnection(
       return await runTestAll(project, io, deps);
     }
 
-    const { driver, detailKey, detailValue } = await testConnectionByDriver(project, args.connectionId, deps);
+    const startedAt = performance.now();
+    let driver = normalizedConnectionDriver(project, args.connectionId) || 'unknown';
+    let detailKey: string;
+    let detailValue: string;
+    try {
+      const outcome = await testConnectionByDriver(project, args.connectionId, deps);
+      driver = outcome.driver;
+      detailKey = outcome.detailKey;
+      detailValue = outcome.detailValue;
+      await emitConnectionTest({
+        project,
+        connectionId: args.connectionId,
+        driver,
+        outcome: 'ok',
+        durationMs: Math.max(0, performance.now() - startedAt),
+        io,
+      });
+    } catch (error) {
+      await emitConnectionTest({
+        project,
+        connectionId: args.connectionId,
+        driver,
+        outcome: 'error',
+        durationMs: Math.max(0, performance.now() - startedAt),
+        error,
+        io,
+      });
+      throw error;
+    }
     io.stdout.write(`Connection test passed: ${args.connectionId}\n`);
     io.stdout.write(`Driver: ${driver}\n`);
     io.stdout.write(`${detailKey}: ${detailValue}\n`);