diff --git a/bin/configure-fastly.js b/bin/configure-fastly.js
index c6f76411d..c3eb4cca2 100644
--- a/bin/configure-fastly.js
+++ b/bin/configure-fastly.js
@@ -24,7 +24,7 @@ var routes = routeJson.map(function (route) {
 
 async.auto({
     version: function (cb) {
-        fastly.getLatestVersion(function (err, response) {
+        fastly.getLatestActiveVersion(function (err, response) {
             if (err) return cb(err);
             // Validate latest version before continuing
             if (response.active || response.locked) {
diff --git a/bin/lib/fastly-extended.js b/bin/lib/fastly-extended.js
index 0e4467221..ffac40acc 100644
--- a/bin/lib/fastly-extended.js
+++ b/bin/lib/fastly-extended.js
@@ -24,11 +24,11 @@ module.exports = function (apiKey, serviceId) {
     };
 
     /*
-     * getLatestVersion: Get the most recent version for the configured service
+     * getLatestActiveVersion: Get the most recent version for the configured service
      *
      * @param {callback} Callback with signature *err, latestVersion)
      */
-    fastly.getLatestVersion = function (cb) {
+    fastly.getLatestActiveVersion = function (cb) {
         if (!this.serviceId) {
             return cb('Failed to get latest version. No serviceId configured');
         }
@@ -37,11 +37,15 @@ module.exports = function (apiKey, serviceId) {
             if (err) {
                 return cb('Failed to fetch versions: ' + err);
             }
-            var latestVersion = versions.reduce(function (lateVersion, version) {
-                if (!lateVersion) return version;
-                if (version.number > lateVersion.number) return version;
-                return lateVersion;
-            });
+            var latestVersion = versions.reduce((latestActiveSoFar, cur) => {
+                // if one of [latestActiveSoFar, cur] is active and the other isn't,
+                // return whichever is active. If both are not active, return
+                // latestActiveSoFar.
+                if (!cur || !cur.active) return latestActiveSoFar;
+                if (!latestActiveSoFar || !latestActiveSoFar.active) return cur;
+                // when both are active, prefer whichever has a higher version number.
+                return (cur.number > latestActiveSoFar.number) ? cur : latestActiveSoFar;
+            }, null);
             return cb(null, latestVersion);
         });
     };
diff --git a/test/unit/lib/fastly-extended.test.js b/test/unit/lib/fastly-extended.test.js
new file mode 100644
index 000000000..451902c16
--- /dev/null
+++ b/test/unit/lib/fastly-extended.test.js
@@ -0,0 +1,160 @@
+describe('fastly library', () => {
+    let mockedFastlyRequest = {};
+
+    jest.mock('fastly', () => (() => ({
+        request: mockedFastlyRequest
+    })));
+    const fastlyExtended = require('../../../bin/lib/fastly-extended'); // eslint-disable-line global-require
+
+    test('getLatestActiveVersion returns largest active VCL number, ' +
+        'when called with VCLs in sequential order', done => {
+        mockedFastlyRequest = jest.fn((method, url, cb) => {
+            cb(null, [
+                {
+                    number: 1,
+                    active: false
+                },
+                {
+                    number: 2,
+                    active: false
+                },
+                {
+                    number: 3,
+                    active: true
+                },
+                {
+                    number: 4,
+                    active: false
+                }
+            ]);
+        });
+        const fastlyInstance = fastlyExtended('api_key', 'service_id');
+
+        fastlyInstance.getLatestActiveVersion((err, response) => {
+            expect(err).toBe(null);
+            expect(response).toEqual({
+                number: 3,
+                active: true
+            });
+            expect(mockedFastlyRequest).toHaveBeenCalledWith(
+                'GET', '/service/service_id/version', expect.any(Function)
+            );
+            done();
+        });
+    });
+
+    test('getLatestActiveVersion returns largest active VCL number, when called with VCLs in mixed up order', done => {
+        mockedFastlyRequest = jest.fn((method, url, cb) => {
+            cb(null, [
+                {
+                    number: 4,
+                    active: false
+                },
+                {
+                    number: 1,
+                    active: false
+                },
+                {
+                    number: 2,
+                    active: true
+                },
+                {
+                    number: 3,
+                    active: false
+                }
+            ]);
+        });
+        const fastlyInstance = fastlyExtended('api_key', 'service_id');
+
+        fastlyInstance.getLatestActiveVersion((err, response) => {
+            expect(err).toBe(null);
+            expect(response).toEqual({
+                number: 2,
+                active: true
+            });
+            expect(mockedFastlyRequest).toHaveBeenCalledWith(
+                'GET', '/service/service_id/version', expect.any(Function)
+            );
+            done();
+        });
+    });
+
+    test('getLatestActiveVersion returns null, when none of the VCL versions are active', done => {
+        mockedFastlyRequest = jest.fn((method, url, cb) => {
+            cb(null, [
+                {
+                    number: 4,
+                    active: false
+                },
+                {
+                    number: 1,
+                    active: false
+                },
+                {
+                    number: 2,
+                    active: false
+                },
+                {
+                    number: 3,
+                    active: false
+                }
+            ]);
+        });
+        const fastlyInstance = fastlyExtended('api_key', 'service_id');
+
+        fastlyInstance.getLatestActiveVersion((err, response) => {
+            expect(err).toBe(null);
+            expect(response).toEqual(null);
+            expect(mockedFastlyRequest).toHaveBeenCalledWith(
+                'GET', '/service/service_id/version', expect.any(Function)
+            );
+            done();
+        });
+    });
+
+    test('getLatestActiveVersion returns largest active VCL number, ' +
+        'when called with a single active VCL', done => {
+        mockedFastlyRequest = jest.fn((method, url, cb) => {
+            cb(null, [
+                {
+                    number: 1,
+                    active: true
+                }
+            ]);
+        });
+        const fastlyInstance = fastlyExtended('api_key', 'service_id');
+
+        fastlyInstance.getLatestActiveVersion((err, response) => {
+            expect(err).toBe(null);
+            expect(response).toEqual({
+                number: 1,
+                active: true
+            });
+            expect(mockedFastlyRequest).toHaveBeenCalledWith(
+                'GET', '/service/service_id/version', expect.any(Function)
+            );
+            done();
+        });
+    });
+
+    test('getLatestActiveVersion returns null, when called with a single inactive VCL', done => {
+        mockedFastlyRequest = jest.fn((method, url, cb) => {
+            cb(null, [
+                {
+                    number: 1,
+                    active: false
+                }
+            ]);
+        });
+        const fastlyInstance = fastlyExtended('api_key', 'service_id');
+
+        fastlyInstance.getLatestActiveVersion((err, response) => {
+            expect(err).toBe(null);
+            expect(response).toEqual(null);
+            expect(mockedFastlyRequest).toHaveBeenCalledWith(
+                'GET', '/service/service_id/version', expect.any(Function)
+            );
+            done();
+        });
+    });
+});