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I'm thinking about starting using KeePass2 with the password database on Dropbox to manage my passwords. I've been doing my research on the subject and I already moved a couple of passwords there to test the waters; so far, so good.

I'm currently stumped on one issue, however. My most important passwords that I definitely want on KeePass are my Google account password and my Dropbox password. But if I store my Dropbox password on KeePass, and KeePass is stored on Dropbox, how would I access my file in the first place to log into Dropbox?

How to people handle this? Do I need to memorize two complex, different passwords (one for KeePass and one for Dropbox) or is there a simple workaround for this I'm just not seeing?

  • Chicken-egg, I guess... (I use lastpass) – Brian Adkins Feb 13 '14 at 20:09
  • On a piece of paper that you put in a safe or some other location with strong physical security controls. – Zoredache Feb 14 '14 at 0:49
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I'll try to help since I use Keepass2.

I recommend you backup your Keepass database, the Master password for it, and the key file in more than one location. One of those locations should be in cold storage.

Don't just store both the Master password and the Key file in Dropbox because if you do forget the password to Dropbox you will lose access to your Keepass database.

Use a flash drive attached to a lanyard with a copy of your Keepass key file on it. This will encourage to you to use it only when you are at your computer.

Create strong password from a sentence that you can remember but add numbers, uppercase letters and symbols. Use this password for your Keepass database. Do the same for Dropbox.

This will prevent you from ever losing your passwords to both Keepass and Dropbox.

  • And where should I store my password database, and how do I keep it synced between devices? – ArmlessJohn Feb 13 '14 at 20:11
  • Sry for the edits, I'm at work and trying to answer your question. "Use a flash drive attached to a lanyard with a copy of your Keepass key file on it. This will encourage to you to use it only when you are at your computer." – Onihonker Feb 13 '14 at 20:25
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Learn your KeePass password. Store your Dropbox password in KeePass. Use a different device such as your smart phone when you want to install Dropbox on a new device.

I have used this setup for ages.

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I am using Keepass on my local storage and with the help of a trigger it is synchronized with dropbox.

Pros :

  • I have always two files
  • It synchronizes entries between files (as the dropbox will be overwritten by dropbox)

Cons :

Here is a copy of the "how to" (but you should have a look at the link to read "how it works")

  1. Create a new directory to use for the Dropbox synchronization, e.g. C:\Documents and Settings\Tom\My Documents\DropboxSync Note: Do not use the current database location, you must have 2 copies of the database.
  2. Copy (do not move) the KeePass database you want to sync to the new directory.
  3. Open KeePass and navigate to 'Tools' -> 'Triggers...'.
  4. Add a trigger.
  5. Call it something meaningful, like "Prevent data loss by Dropbox".
  6. Navigate to the 'Events' tab and add an event.
  7. Select 'Saved database file'.
  8. If you only want to sync a certain database, set the 'File/URL - Comparison' to 'Equals' and the 'File/URL - Filter' field to the required database file path. Otherwise don't change the fields.
  9. Navigate to the 'Action' tab and add a new action.
  10. Select 'Change trigger on/off state'.
  11. Leave the 'Trigger name' field empty.
  12. In the 'New state' field change the state to 'Off'.
  13. Click 'OK' to save the action.
  14. Add a new action.
  15. Select 'Synchronize active database with a file/URL'.
  16. Enter the full path and name of your copy of the KeePass database in the 'File/URL' field, e.g. C:\Documents and Settings\Tom\My Documents\DropboxSync\MyDatabase.kdbx
  17. Click 'OK' to save the action.
  18. Add a new action.
  19. Select 'Change trigger on/off state'.
  20. Leave the 'Trigger name' field empty.
  21. In the 'New state' field change the state to 'On'.
  22. Click 'OK' to save the action.
  23. Save the event.
  24. Set Dropbox to synchronize the database in the Dropbox sync directory.
  25. Perform these steps on all PCs that you will sync with Dropbox.
  • always two files kdbx ? – Kiquenet Oct 13 '16 at 9:22
  • Yes one file to be managed / written by dropbox whenever he wants. And one local file, This way you let keepass resolve conflicts as dropbox won't do anything about it and will just overwrite the full file – Christ-OFF Oct 14 '16 at 7:34
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You'll notice that Keepass2 asks you for a key file in addition to or instead of a password.

Some strategies you could implement:

  • Have a simpler, easily memorizable but relatively decent password and select a random file (image, etc.) on your desktop that only you know is the key file for your kdbx.

  • Have no password and a keyfile made of purely random numbers (use a generator to create such a file), or other file, and place this keyfile on an external drive you can keep physically secure.

I would at least use a very simple password in any case.

The keyfile may present problems if you want to view the database on your phone, but if your phone has an SD card or other easy way to get files in it, you could work something out.

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I don't really get the question. As long as you have DropBox software installed in a couple of locations, the files will be synchronised to those computers. So there is no need to worry abou the DropBox password, if something happens to it, you still have the locally synch'd copies to work with.

This gets better still when using with a mobile device. You can have another copy there.

So you always have copies of your KeePass database. As long as you remember the password for that, there is nothing else to do.

Personally, I use LastPass for low-medium risk IDs and passwords, KeePass for high-risk and for a copy of the LastPass entries. LastPass is used for convenience. LastPass is also available on multiple devices so all my password databases are in multiple locations - I can't afford to loose them.

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Extending on the answer by Christ-OFF:

Have your local file synchronised to Drop-Box, so you always have a local copy to find your Drop-Box password. I synchronise between 3 devices with Drop-Box:

  1. Home PC (Ubuntu with KeePassX)
  2. Work PC
  3. SmartPhone (Android with Keepass2Android)

I also have multiple databases:

  1. Work
  2. Private

NB: See the {DB_NAME} variable variation in the trigger setup below to handle this!!

Pros :

  • I always have multiple copies of files
  • KeePass synchronizes entries between files (as the dropbox will be overwritten by dropbox)

Cons :

Here is a copy of the "how to" with my variations (but you should have a look at the link to read "how it works")

  • Create a new directory to use for the Dropbox synchronization, e.g. C:\Users\Tom\Dropbox Note: Do not use the current database location, you must have 2 copies of the database.
  • Copy (do not move) the KeePass database you want to sync to the new directory.
  • Open KeePass and navigate to 'Tools' -> 'Triggers...'.
  • Add a trigger.
  • Call it something meaningful, like "DropboxSync" and note this for after.
  • Navigate to the 'Events' tab and add an event.
  • Select 'Saved database file'.
  • If you only want to sync a certain database, set the 'File/URL - Comparison' to 'Equals' and the 'File/URL - Filter' field to the required database file path. Otherwise don't change the fields.
  • Add a second event, select 'Opened database file'. As before, leave the 'File/URL' empty unless you only want to sync a certain database.
  • Navigate to the 'Action' tab and add a new action.
  • Select 'Change trigger on/off state'.
  • Leave the 'Trigger name' field empty.
  • In the 'New state' field change the state to 'Off'.
  • Click 'OK' to save the action.
  • Add a new action.
  • Select 'Synchronize active database with a file/URL'.
  • Enter the path to the Drop-Box folder and use the KeePass variable {DB_NAME} in the 'File/URL' field, e.g. C:\Users\Tom\Dropbox{DB_NAME}
  • Click 'OK' to save the action.
  • Add a new action.
  • Select 'Change trigger on/off state'.
  • Leave the 'Trigger name' field empty (or enter this trigger's name 'DropboxSync' if you don't want to reactivate all).
  • In the 'New state' field change the state to 'On'.
  • Click 'OK' to save the action.
  • Save the event.
  • Set Dropbox to synchronize the database in the Dropbox sync directory.
  • Perform these steps on all PCs that you will sync with Dropbox.

Many thanks to the developers!! :-)

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Assuming you're going to need to memorise at least one password, why not make the KeePass (or Dropbox) password simpler?

Make a Dropbox specifically (and only) for your KeePass database which has a complex password, then keep a simpler password on your database. This will give you a decent compromise to the need to memorise two complex passwords but still keep your database sufficiently secure.

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