diff --git a/package.json b/package.json
index 0d329ac8..3e4ab7d7 100644
--- a/package.json
+++ b/package.json
@@ -17,6 +17,7 @@
     "inquirer": "^7.1.0",
     "qs": "^6.9.3",
     "semver": "^7.3.0",
+    "tslib": "~1.11.2",
     "tsv": "^0.2.0",
     "twilio": "^3.43.1"
   },
diff --git a/src/services/require-install.js b/src/services/require-install.js
index 59c093ac..ba6e302f 100644
--- a/src/services/require-install.js
+++ b/src/services/require-install.js
@@ -94,16 +94,16 @@ const requireInstall = async (packageName, command) => {
   }
 
   // If we're here, attempt to install the package in the plugin's runtime modules path.
-  try {
-    logger.warn(`Installing ${packageName} ...`);
-    const packageTag = targetVersion ? `${packageName}@${targetVersion}` : packageName;
-    const plugins = new Plugins({ dataDir: pluginPath, cacheDir: pluginPath });
+  logger.warn(`Installing ${packageName} ...`);
+  const plugins = new Plugins({ dataDir: pluginPath, cacheDir: pluginPath });
 
+  try {
     // Init the PJSON in case it doesn't exist. This is required by yarn or it
     // moves up the dir tree until it finds one.
     await plugins.createPJSON();
 
     // Force install the package in case it's a native module that needs rebuilding.
+    const packageTag = targetVersion ? `${packageName}@${targetVersion}` : packageName;
     await plugins.yarn.exec(['add', '--force', packageTag], { cwd: pluginPath, verbose: false });
   } catch (error) {
     logger.debug(`Error installing ${packageName}: ${error}`);
diff --git a/test/services/require-install.test.js b/test/services/require-install.test.js
index 0254dfeb..c7eaae48 100644
--- a/test/services/require-install.test.js
+++ b/test/services/require-install.test.js
@@ -1,6 +1,7 @@
 const tmp = require('tmp');
 const { expect, test } = require('@twilio/cli-test');
 const { getCommandPlugin, getPackageVersion, getDependencyVersion, checkVersion, requireInstall } = require('../../src/services/require-install');
+const { logger, LoggingLevel } = require('../../src/services/messaging/logging');
 const corePJSON = require('../../package.json');
 
 const TOP_PLUGIN = {
@@ -95,13 +96,24 @@ describe('services', () => {
     });
 
     describe('requireInstall', () => {
+      before(() => {
+        logger.config.level = LoggingLevel.debug;
+      });
+
+      after(() => {
+        logger.config.level = LoggingLevel.info;
+      });
+
       test.it('can load existing packages', () => {
         expect(requireInstall('chai')).to.not.be.undefined;
       });
 
-      test.it('will attempt to install packages', async () => {
+      test.stderr().it('will attempt to install packages', async ctx => {
         const command = { id: 'top-command', config };
         await expect(requireInstall('chai-dai', command)).to.be.rejected;
+        expect(ctx.stderr).to.contain('Error loading chai-dai');
+        expect(ctx.stderr).to.contain('Installing chai-dai');
+        expect(ctx.stderr).to.contain('Error installing chai-dai');
       });
     });
   });