When comparing Cloak vs LastPass, the Slant community recommends Cloak for most people. In the question“What are the best power user tools for macOS?” Cloak is ranked 29th while LastPass is ranked 35th. The most important reason people chose Cloak is:
SSL pinning protects against some forms of man-in-the-middle attacks that even SSL encrypted traffic is vulnerable to. Not long ago, iOS did not allow for pinning but that may have changed more recently.
Specs
Question Ranking
Pros
Pro Does SSL Pinning on OS X
SSL pinning protects against some forms of man-in-the-middle attacks that even SSL encrypted traffic is vulnerable to. Not long ago, iOS did not allow for pinning but that may have changed more recently.
Pro Responsive developer
The developer of Cloak is extremely responsive to feedback and quick to answer questions or support requests.
Pro Senses Trusted WiFi networks
Cloak can be set to not use the VPN on whitelisted WiFI SSIDs (like home/work).
Pro Unlimited devices (as long as they're OSX/iOS)
Unlimited devices and data per account, so you can connect up the whole family or office on one account if you so choose.
Pro Automatic cloud backup and cross-device sync
LastPass keeps an encrypted copy of all passwords locally as well as an encrypted copy on their servers. That way, passwords can be accessed locally while offline, or through their server while online from any machine.
Pro Seamless autofill and password generator via plugins for all popular browsers
All common browsers, including Opera, have plugins that allow automatically filling in forms and generating passwords. All form fill information syncs across all platforms, devices and browsers. Password generator can be adjusted to use or exclude certain characters and patterns.
Pro Multifactor authentication
LastPass offers multiple multifactor authentication options, including Google Authenticator, Grid Multifactor Authentication, Microsoft Authenticator App, Toopher Authentication, Duo Security Authentication, Transakt Authentication, Sesame Multifactor Authentication, Smart Card Authentication and Yubikey Multifactor Authentication.
Pro All encryption and decryption is done locally
All the encryption and decryption is done by the client (JS/App) so even LastPass doesn't have access to passwords.
Pro Has a free tier and a cheap premium tier
LastPass offers a free tier. The paid tier ($1/mo) adds unlimited use of LastPass mobile apps, more multifactor authentication options, ad-free and priority assistance and tools for locked-down computers.
Pro Works on Linux
LastPass alongside KeePassX are the only cloud-syncing password managers that work on Linux.
Pro Works with portable versions of Chrome and Firefox
Firefox 2+ on Windows, Mac & Linux as well as Chrome 4+ on Windows and Linux support a portable version of LastPass. Great for securely accessing LastPass Vault from public or untrusted computers.
Pro Automatic security monitoring
LastPass will check for re-used and unsafe passwords.
Pro Clean and intuitive UI
Since version 3.0 the LastPass interface is clean and easy to navigate on all platforms.
Pro Does not require a standalone app
While many password managers require a standalone app to be installed on the system, LastPass does not and can function via browser plugins.
Pro Fingerprint verification
Some fingerprint readers, like TouchID on iOS devices or on Samsung devices, can be set up to be used to access LastPass instead of a master password.
Pro Allows sharing passwords with one person or a group of people
LastPass allows sharing login data for a site with another user of LastPass without exposing the password. Great for allowing friends, family or coworkers access a site.
Pro Offers multiple export options
LastPass can dump the whole database as a .csv file or an encrypted file that can then be decrypted using LastPass Pocket as well as separately export Wi-Fi passwords and autofill information. Additional export options are available on a per-browser basis.
Pro Can create one-time passwords for accessing the Vault
LastPass allows creating passwords for accessing the LastPass Vault that can only be used once. Great for accessing the Vault in public or untrusted places.
Pro Yubikey Support
LastPass offers multifactor authentication via Yubikey.
Pro Password One-Click Change
LastPass is able to change your password automagically.
Pro Allows downloading an encrypted database backup that can only be decrypted with LastPass Pocket
LastPass Pocket is a standalone personal database decrypter. It's a portable executable, meaning it does not need to be installed, that is used to decrypt a local encrypted copy of the password database.
Pro Vetted by Steve Gibson
Steve Gibson is a well established security researcher best know for his work with Apple and Atari systems as well as founding Gibson Research Corporation. He was given access to LastPass' source code and confirmed that it's safe to trust its security.
Pro Military grade encryption
Lastpass has 256-bit AES encryption implemented in C++ and JavaScript with one-way salted hashes.
Pro Works even with browsers that don't support plugins
Via a clever use of bookmarklets, LastPass works on browsers that don't inherently support bookmarklets, like Opera or Safari on iOS.
Pro Credit monitoring in US
LastPass can be set to notify if a user's credit report suddenly changes.
Pro Works with Windows applications with native app
Can record the steps and use it to login to native Windows apps.
Cons
Con Hasn't published server/data center locations
Con OSX & iOS Only, without even manual configuration instructions for Linux/Windows
Con Not free/libre
This application is proprietary, and thus cannot be modified, freely distributed, or trusted to be secure.
Con Forced cloud backup
The is no way to opt-out of saving all of passwords on LastPass servers.
Con When generating passwords, LastPass tends to put the wrong info in forms
For forms with both an email address and username, LastPass tends to mix up and overwrite information.
Con History of bad support for the company behind LastPass
You never know how much you will pay for it because LogMeIn did the same with Hamachi product. Support will be bad.
Con Somewhat poor customer service
LastPass maintains a support forum which they mostly ignore, labeling it "mostly peer-to-peer support" leaving only their e-mail ticket system to turn to.
Con Forgets to ask "add new site?" on some websites
So you are forced to add a new site manually, which takes too long (relatively speaking).
Con Doesn't always log out when idle
This issue is especially common with the mobile app.
Con Mobile apps are not intuitive
Con Has been hacked before
And becomes extra bad as you are forced to have everything at a one central cloud place.