diff --git a/lib/commands/update.js b/lib/commands/update.js
index fe9c60560..0c4785d68 100644
--- a/lib/commands/update.js
+++ b/lib/commands/update.js
@@ -76,15 +76,7 @@ class UpdateCommand extends Command {
             }, {
                 title: 'Updating to a major version',
                 task: majorUpdate,
-                // CASE: Skip if you are already on ^2 or you update from v1 to v1.
-                enabled: () => {
-                    if (semver.major(instance.version) === 2 ||
-                        semver.major(context.version) === 1) {
-                        return false;
-                    }
-
-                    return true;
-                }
+                enabled: () => semver.major(context.version) > semver.major(instance.version)
             }, {
                 title: 'Stopping Ghost',
                 enabled: () => isRunning,
@@ -103,14 +95,7 @@ class UpdateCommand extends Command {
                 // CASE: We have moved the execution of knex-migrator into Ghost 2.0.0.
                 //       If you are already on v2 or you update from v1 to v2, then skip the task.
                 //       We compare the major versions, otherwise pre-releases won't match.
-                enabled: () => {
-                    if (semver.major(instance.version) === 2 ||
-                        semver.major(context.version) === 2) {
-                        return false;
-                    }
-
-                    return true;
-                }
+                enabled: () => semver.major(context.version) < 2
             }, {
                 title: 'Restarting Ghost',
                 enabled: () => argv.restart,
@@ -182,17 +167,12 @@ class UpdateCommand extends Command {
         const semver = require('semver');
 
         return fs.readdir(path.join(process.cwd(), 'versions')).then((versions) => {
-            versions = versions.filter(semver.valid);
+            versions = versions.filter(semver.valid).sort(semver.compare);
             if (versions.length <= 5) {
                 task.skip();
                 return;
             }
 
-            // eslint-disable-next-line arrow-body-style
-            versions.sort((a, b) => {
-                return semver.lt(a, b) ? -1 : 1;
-            });
-
             const promises = versions.slice(0, -5)
                 .map(version => fs.remove(path.join(process.cwd(), 'versions', version)));
 
diff --git a/lib/process-manager.js b/lib/process-manager.js
index 9c2fbafc6..1c80c7c7e 100644
--- a/lib/process-manager.js
+++ b/lib/process-manager.js
@@ -69,7 +69,7 @@ class ProcessManager {
             stopOnError: true,
             port: this.instance.config.get('server.port'),
             host: this.instance.config.get('server.host', 'localhost'),
-            useNetServer: semver.major(this.instance.version) === 2
+            useNetServer: semver.major(this.instance.version) >= 2
         }, options || {});
 
         try {
diff --git a/lib/tasks/migrator.js b/lib/tasks/migrator.js
index d232eec7e..7682f6672 100644
--- a/lib/tasks/migrator.js
+++ b/lib/tasks/migrator.js
@@ -91,7 +91,7 @@ module.exports.rollback = function runRollback(context) {
 
     // Ghost 2.0.0 uses the new knex-migrator version. We have to ensure you can still use CLI 1.9 with an older blog, because
     // we haven't restricted a CLI version range in Ghost (we only used cli: > X.X.X)
-    if (semver.major(version) === 2) {
+    if (semver.major(version) >= 2) {
         args = ['--force', '--v', previousVersion, '--mgpath', currentDir];
     } else {
         args = ['--force', '--mgpath', currentDir];