diff --git a/packages/cli/snapshots/integration/snapshot-matcher/suite-first-run.integration.snapshots.js b/packages/cli/snapshots/integration/snapshot-matcher/suite-first-run.integration.snapshots.js
new file mode 100644
index 000000000000..e8f724f91d11
--- /dev/null
+++ b/packages/cli/snapshots/integration/snapshot-matcher/suite-first-run.integration.snapshots.js
@@ -0,0 +1,17 @@
+// IMPORTANT
+// This snapshot file is auto-generated, but designed for humans.
+// It should be checked into source control and tracked carefully.
+// Re-generate by setting UPDATE_SNAPSHOTS=1 and running tests.
+// Make sure to inspect the changes in the snapshots below.
+// Do not ignore changes!
+
+'use strict';
+
+exports[`snapshot-matcher first case matches snapshot 1`] = `
+first case
+`;
+
+
+exports[`snapshot-matcher first case shared test matches snapshot 1`] = `
+common result
+`;
diff --git a/packages/cli/snapshots/integration/snapshot-matcher/suite-second-run.integration.snapshots.js b/packages/cli/snapshots/integration/snapshot-matcher/suite-second-run.integration.snapshots.js
new file mode 100644
index 000000000000..c16c599ebdc5
--- /dev/null
+++ b/packages/cli/snapshots/integration/snapshot-matcher/suite-second-run.integration.snapshots.js
@@ -0,0 +1,17 @@
+// IMPORTANT
+// This snapshot file is auto-generated, but designed for humans.
+// It should be checked into source control and tracked carefully.
+// Re-generate by setting UPDATE_SNAPSHOTS=1 and running tests.
+// Make sure to inspect the changes in the snapshots below.
+// Do not ignore changes!
+
+'use strict';
+
+exports[`snapshot-matcher second case matches snapshot 1`] = `
+second case
+`;
+
+
+exports[`snapshot-matcher second case shared test matches snapshot 1`] = `
+common result
+`;
diff --git a/packages/cli/test/integration/snapshot-matcher/common.suite.js b/packages/cli/test/integration/snapshot-matcher/common.suite.js
new file mode 100644
index 000000000000..5c346fff2929
--- /dev/null
+++ b/packages/cli/test/integration/snapshot-matcher/common.suite.js
@@ -0,0 +1,21 @@
+// Copyright IBM Corp. 2018,2020. All Rights Reserved.
+// Node module: @loopback/cli
+// This file is licensed under the MIT License.
+// License text available at https://opensource.org/licenses/MIT
+
+'use strict';
+
+// A shared test suite executed by "suite-first-run.integration.js"
+// and "suite-second-run.integration.js"
+const {expectToMatchSnapshot} = require('../../snapshots');
+
+/**
+ * Execute this method from inside a `describe()` block in your test file.
+ */
+exports.commonTestSuite = function () {
+  describe('shared test', () => {
+    it('matches snapshot', function () {
+      expectToMatchSnapshot('common result');
+    });
+  });
+};
diff --git a/packages/cli/test/integration/snapshot-matcher/suite-first-run.integration.js b/packages/cli/test/integration/snapshot-matcher/suite-first-run.integration.js
new file mode 100644
index 000000000000..42dcde6000b2
--- /dev/null
+++ b/packages/cli/test/integration/snapshot-matcher/suite-first-run.integration.js
@@ -0,0 +1,17 @@
+// Copyright IBM Corp. 2018,2020. All Rights Reserved.
+// Node module: @loopback/cli
+// This file is licensed under the MIT License.
+// License text available at https://opensource.org/licenses/MIT
+
+'use strict';
+
+const {expectToMatchSnapshot} = require('../../snapshots');
+const {commonTestSuite} = require('./common.suite');
+
+describe('snapshot-matcher first case', () => {
+  commonTestSuite();
+
+  it('matches snapshot', () => {
+    expectToMatchSnapshot('first case');
+  });
+});
diff --git a/packages/cli/test/integration/snapshot-matcher/suite-second-run.integration.js b/packages/cli/test/integration/snapshot-matcher/suite-second-run.integration.js
new file mode 100644
index 000000000000..019c8c018c64
--- /dev/null
+++ b/packages/cli/test/integration/snapshot-matcher/suite-second-run.integration.js
@@ -0,0 +1,17 @@
+// Copyright IBM Corp. 2018,2020. All Rights Reserved.
+// Node module: @loopback/cli
+// This file is licensed under the MIT License.
+// License text available at https://opensource.org/licenses/MIT
+
+'use strict';
+
+const {expectToMatchSnapshot} = require('../../snapshots');
+const {commonTestSuite} = require('./common.suite');
+
+describe('snapshot-matcher second case', () => {
+  commonTestSuite();
+
+  it('matches snapshot', () => {
+    expectToMatchSnapshot('second case');
+  });
+});
diff --git a/packages/cli/test/snapshot-matcher.js b/packages/cli/test/snapshot-matcher.js
index 17b841d3f6a5..6351e20339fe 100644
--- a/packages/cli/test/snapshot-matcher.js
+++ b/packages/cli/test/snapshot-matcher.js
@@ -16,8 +16,11 @@ move this file to a standalone package so that all Mocha users can use it.
 
 const chalk = require('chalk');
 const assert = require('assert');
+const debug = require('debug')('test:snapshot-matcher');
 const path = require('path');
 
+const root = process.cwd();
+
 module.exports = {
   initializeSnapshots,
 };
@@ -43,6 +46,22 @@ module.exports = {
  * ```
  */
 function initializeSnapshots(snapshotDir) {
+  if (debug.enabled) {
+    const stack = new Error().stack
+      .split(/\n/g)
+      // Remove the error message and the top stack frame pointing to ourselves
+      // and pick three frames (max), that should be enough to identify
+      // which test file called us.
+      .slice(2, 5)
+      .map(f => `\n${f}`)
+      .join();
+    debug(
+      'Initializing snapshot matcher, storing snapshots in %s%s',
+      snapshotDir,
+      stack,
+    );
+  }
+
   let currentTest;
   let snapshotErrors = false;
 
@@ -101,8 +120,10 @@ function matchSnapshot(snapshotDir, currentTest, actualValue) {
   const key = buildSnapshotKey(currentTest);
 
   if (!(key in snapshotData)) {
+    const shortFile = path.relative(root, snapshotFile);
     throw new Error(
-      `No snapshot found for ${JSON.stringify(key)}.\n` +
+      `No snapshot found in ${JSON.stringify(shortFile)} ` +
+        `for ${JSON.stringify(key)}.\n` +
         'Run the tests with `UPDATE_SNAPSHOTS=1` environment variable ' +
         'to create and update snapshot files.',
     );
@@ -129,6 +150,13 @@ function recordSnapshot(snapshots, currentTest, actualValue) {
 
   const key = buildSnapshotKey(currentTest);
   const testFile = currentTest.file;
+  if (debug.enabled) {
+    debug(
+      'Recording snapshot %j for test file %j',
+      key,
+      path.relative(root, testFile),
+    );
+  }
   if (!snapshots[testFile]) snapshots[testFile] = Object.create(null);
   snapshots[testFile][key] = actualValue;
 }
@@ -211,6 +239,7 @@ function writeSnapshotData(snapshotFile, snapshots) {
 
   const content = header + entries.join('\n');
   mkdirp.sync(path.dirname(snapshotFile));
+  debug('Updating snapshot file %j', path.relative(root, snapshotFile));
   return writeFileAtomic(snapshotFile, content, {encoding: 'utf-8'});
 }