diff --git a/lib/pip.js b/lib/pip.js
index ccb809c3..149c0285 100644
--- a/lib/pip.js
+++ b/lib/pip.js
@@ -412,6 +412,16 @@ async function installRequirements(targetFolder, pluginInstance) {
             'PYTHON_REQUIREMENTS_COMMAND_NOT_FOUND'
           );
         }
+
+        if (cmd === 'docker' && e.stderrBuffer) {
+          throw new pluginInstance.serverless.classes.Error(
+            `Running "${cmd} ${args.join(' ')}" failed with: "${e.stderrBuffer
+              .toString()
+              .trim()}"`,
+            'PYTHON_REQUIREMENTS_DOCKER_COMMAND_FAILED'
+          );
+        }
+
         if (log) {
           log.info(`Stdout: ${e.stdoutBuffer}`);
           log.info(`Stderr: ${e.stderrBuffer}`);
diff --git a/test.js b/test.js
index 0ecd361d..26b4b477 100644
--- a/test.js
+++ b/test.js
@@ -216,6 +216,7 @@ test(
         dockerImage: 'break the build to log the command',
       },
     });
+    console.log('STDOUT', stdout);
     t.true(
       stdout.includes(
         `-v ${__dirname}${sep}tests${sep}base${sep}custom_ssh:/root/.ssh/custom_ssh:z`