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Dropbox Terms

When in the course of network events rumors start flying about Dropbox a decent respect for the concerns of 1Password users compels me to blog about it.

1Password users certainly enjoy the convenience of syncing their data across Mac, Windows, iPhone, iPad, iPod Touch, Android and Windows 7 Phone. This is managed using Dropbox, and so it is fit and proper for 1Password users to be attuned to news regarding Dropbox security and privacy.

1Password in DropboxYesterday (July 1) Dropbox provided an update of their terms of service. Since then the net has been a-twitter with very frightening accusations about what Dropbox may do with your data. Those accusations are incorrect, and the Dropbox terms of service do not give them any rights to your data that you wouldn’t expect. And as always the main thing to keep in mind is that your 1Password data are well encrypted before ever being sent to Dropbox (or even written to your own disk).

Read the policy, not the tweets

It appears some misleading (at best) and downright incorrect claims about the Dropbox Terms of Service are spreading via Twitter and blogs. So don’t trust what the bloggers say (I guess that includes me) and go read the Dropbox Terms for yourself.

Permission to share what you ask them to share

The portion that seems to be behind the panic is in this paragraph:

We sometimes need your permission to do what you ask us to do with your stuff (for example, hosting, making public, or sharing your files). By submitting your stuff to the Services, you grant us (and those we work with to provide the Services) worldwide, non-exclusive, royalty-free, sublicenseable rights to use, copy, distribute, prepare derivative works (such as translations or format conversions) of, perform, or publicly display that stuff to the extent reasonably necessary for the Service. This license is solely to enable us to technically administer, display, and operate the Services. You must ensure you have the rights you need to grant us that permission. [Emphasis added]

Dropbox can be used for more than just syncing your own private data. It can be used to share information with selected others or with the world. When you put something in your Public folder on Dropbox to share, you are asking Dropbox to re-publish that data. Dropbox actually needs your permission to do so, and this paragraph is the bit of their Terms of Service which allows them to share the material you ask them to share.

The bottom line is that there is nothing in these Dropbox Terms of Service that gives them the right to do anything with your data that you don’t ask them to do. (The one exception is in the paragraph of the Dropbox privacy policy which states that they will comply with law enforcement requests for data stored on Dropbox.)

New Security Document

I have complained in the past that Dropbox had been unclear about their security policy with respect to everyone’s data. I am very pleased that they have produced a new security document now and that they took the time to do it right. It contains no surprises. Also with this announcement, they have updated their applications and APIs for mobile devices to address an earlier concern about encrypted filenames and such.

Why Dropbox and where are the alternatives?

Dropbox seems to have shifted from an Internet darling to a boogyman in less than six months. The silly accusations regarding re-publishing permissions in their newly stated Terms of Service illustrates that any allegation about them will gain traction even when completely unfounded. But even though this current hysteria can be dismissed it doesn’t mean that we can brush off all concerns about Dropbox or any cloud syncing solution.

I will try to briefly address some of the questions that come up in any discussion of Dropbox and 1Password. These are “Why Dropbox?” and “Have you considered X as an alternative sync solution?”

Dropbox does two things that no other system (yet) does. It provides the necessary programming tools (APIs) for all of the platforms that we support: OS X, Windows, iOS, Android, and Windows 7 Phone; and it provides syncing to truly native filesystems on the Mac and PC.

The short answer to “Have you considered X as an alternative sync solution” is “Yes” for every value of X that people have asked about. We have considered them, and have had to reject them for various technical reasons.

Getting more technical

Each item in your 1Password data is stored in its own, separate, file. This is great for syncing in that it means that only the changes need to sync and this can be done by file and folder syncing. This not only makes syncing faster and cheaper, it also makes it much more reliable and robust against potential data corruption. But this also means that 1Password needs to read lots of different files quickly as it runs. Dropbox does fast syncing while storing the local files on the native local file systems, allowing it to function properly.

As an illustration, an alternative such as WebDAV (which we worked on extensively but had to abandon before we moved to Dropbox) provides a file system abstraction layer that is just too slow for 1Password. It can hang when we try to access some file that it hasn’t cached properly. Also WebDAV isn’t designed for updating many files is quick succession. It’s not that WebDAV is bad, but it isn’t suitable for how we would use it.

Everything else we’ve looked at (and we have looked at many things) suffers not only from the same problems we saw with WebDAV, but they also lack usable APIs for all the platforms we need to support. It may be possible, for example, to sync data to an Android or iOS device using SugarSync or Wuala, but it isn’t possible to sync that data in a way that would make it available to 1Password on those devices.

What’s gone before

I’ve written about a number of things related to the security of your 1Password data in the cloud and on Dropbox in particular. Instead of repeating those, I will list some of those here.

Dropbox Security Questions and Dropbox security revisited: Plus ça change
Both discuss the Dropbox security issues that arose earlier this year. As an update, over the course of the past few months, Dropbox have successfully addressed each of those concerns.
Defending against crackers: Peanut Butter Keeps Dogs Friendly, Too.
What we do to defend your master password against automated crackers if your data should fall into the wrong hands.
Toward Better Master Passwords
What you can do to defend your master password against automated crackers if your data should fall into the wrong hands.
Looking ahead in security
Some hints about what we are working on to make your data even more secure in the cloud.

In Conclusion

Thinking about security (and privacy) is hard. It is important to look at the facts behind the headlines and the tweets before jumping to conclusions.

Update: An expert weighs in

Simon Bradshaw who blogs about intellectual property and technology on his LawClanger blog has posted an analysis, coming to pretty much the same conclusions presented above. [Updated, July 5]

Update 2: Dropbox rewrites

On July 6, Dropbox posted about a rewrite of their Terms of Service. In my reading of it, it makes no changes of substances, but it goes above and beyond the standard language that we see elsewhere in allaying fears.

By using our Services you provide us with information, files, and folders that you submit to Dropbox (together, “your stuff”). You retain full ownership to your stuff. We don’t claim any ownership to any of it. These Terms do not grant us any rights to your stuff or intellectual property except for the limited rights that are needed to run the Services, as explained below. [...]

Now that things have calmed down a bit, I would like to reflect on (and rant about) how we got here.

My overall point remains. A few people who were unfamiliar with reading ToSes delved into the earlier ToS and misinterpreted something and posted their misinterpretations. Those misinterpretations spread like wildfire because others were willing to believe the worst instead of investigating for themselves. I am not criticizing typical users for doing so, but my frustration is directed at portions of the technology press who did not do their job.

People are correct to be concerned about what is buried in Terms of Service and Privacy agreements. As a whole, we don’t pay enough attention to these, and it is good news that people are paying more attention. But it also takes some time to learn how to read them. If something seems fishy, ask for an explanation before jumping to the conclusion that something is evil. If you are part of the technology press your job is to do your homework instead of just regurgitating hot stories for clicks. The press’ job is to investigate, analyze and explain. [Updated July 8]

Toward Better Master Passwords

1Password is great for generating strong random passwords for sites without you ever having to memorize (or even see) those passwords. But there are a few passwords that we all do need to remember. I have a small number (I wish I could say just one) high security passwords that I need to remember. One, of course, is my 1Password master password.

Your 1Password master password is extremely important. Although we take steps to thwart automated password crackers you should still use a strong, memorable master password. Password cracking tools are becoming more powerful every year, and too much is at stake in your 1Password data. Given the strength of the encryption we use, your master password is likely to be the weakest link in your 1Password security. Don’t be too scared of that. Given how strong everything else is, it would be practically impossible to use and remember a master password that is actually stronger than 1Password’s encryption.

This is going to be a very long blog post, so I’d like to start out with a few points to keep in mind

  1. We are not seeking perfection. Instead we need to find ways to improve master passwords if they aren’t currently very strong.
  2. Many of the schemes that people (including myself) have proposed in the past suffer from a major flaw.
  3. No matter what you read here, always keep in mind that a master password that you can’t type or remember is terrible choice of master password.
  4. This discussion applies only to 1Password data on the desktops or stored in the cloud. Master passwords for 1Password on iOS do not need to be as strong as master passwords on the desktops. [Update: Since 1Password 4 for iOS was introduced in December 2012, the same Master Password is used on all of your devices.]

Change a weak master password, otherwise leave it be

Change master password window

We’ve all been told to change passwords on a regular basis, and there are still some circumstances under which that remains reasonable advice. But it is not a good idea with 1Password master passwords. Ideally you should pick a good master password at the outset and never change it.

Passwords in need of changing

Everybody knows to avoid short, common passwords or dictionary words (in any language). The world’s most common password, 123456, is, of course, terrible. But even things like Sally4th or like Molly&Patty2 (the names of my dogs) are not really strong enough for something as important as your 1Password data. The latter is just of the form NAME & NAME DIGITS which password guessing programs do get around to checking.

You can change your master password in 1Password by going to Preferences > Security and clicking on the “Change Master Password” button.

After you change your master password

It is extremely important that you learn your new master password, and you learn it through practice.
Go to the Security preference pane again and set “Auto-Lock” on and to a short time. Maybe just 5 or 10 minutes. This will mean that you will have to type in your master password more frequently, but that will help you learn it. After a few days, you can then set the Auto-lock time back to something less annoying.

Also – and this may sound like heresy even though it is sound security advice – when you change your master password, you can write it down on a slip of paper and put it in your wallet. Once you no longer need to refer to it, you can destroy the piece of paper.

A walk through of a password creation system

The challenge that we face is to have master passwords that not going to be guessed by password cracking programs, yet we mere mortals are capable of remembering and typing without it being a burden.

What makes this a particular challenge is the fact that the bad guys know at least as much about how people pick passwords as we do. They are not only reading the same password picking advice that gets posted in places like this, but they have studied millions of stolen passwords.

Here is an important principle that we need to keep in mind:

The strength of a password creation system is not how many letters, digits, and symbols you end up with, but how many ways you could get a different result using the same system.

Don’t worry if this principle doesn’t make sense yet. It will should start to after I walk through an example.

I have two dogs: Molly and Patty. Suppose I wanted to make a master password from that and came up with Ihave2dogs:Molly&Patty. With that as an example, I’ll work through why that isn’t as good as it might first appear. (It looks good at first because it is long, has mixed case, and has punctuation.)

Use spaces to make things easier for you

1Password master passwords can include spaces. So you can make things easier to type and remember by using spaces (even though it adds little to the actual security). So our first improvement will be to change this to I have 2 dogs: Molly & Patty

Don’t tell the the truth

If your master password is to be based on something meaningful, remember that there are more ways to lie than to tell the truth. There are more ways for me to lie about my pets than tell the truth, and so I should use a lie. So let’s try, I have 3 bats: Larry, Moe & Curly.

Don’t make sense

There are more ways for a sentence to not make sense than to make sense. So let’s change my three bats to thirty-five bats, but still list three: I have 35 bats: Larry, Moe & Curly

Avoid predictable phrases

For those of us of a certain age and steeped in American culture, once we begin a list of names with “Larry…” following it with “Moe and Curly” is very predictable. So even though the Moe & Curly add 11 characters to the password, those 11 characters are so predictable that they add very little actual strength. Even though it is shorter, using I have 35 bats: Larry & Amy is actually stronger than I have 35 bats: Larry, Moe & Curly.

Along the same lines, the “e” after “I hav” isn’t doing much good either. Because it is easily guessable from the rest of the password it isn’t actually adding much strength. There is nothing wrong with that “e”, but I’m mentioning it to help illustrate the point that the number of ways things can be different is often more important than length itself.

Avoid secrets or things that are personally meaningful

The more personally meaningful something is to you the fewer alternatives there are. There are more things that don’t have personal meaning to you than do.

In particular avoid personal secrets. Twice in my life when I’ve been asked to find weak passwords where I worked, I had the embarrassing task of telling my friends and colleagues to change passwords that also revealed their secret crushes. Also there may be a time when you actually do need to reveal your master password to a loved one. When I spot passwords like IloveUVicky along with the owner’s email address among 26000 email addresses and password exposed from a pornography site, I certainly hope that this won’t cause too much trouble for the owner.

Obvious punctuation is obvious

Capitalizing the beginnings of words or changing “for” to “4” really doesn’t add much security. Remember, if you can think to do this, the people who write password cracking systems have already done the same. Unfortunately adding punctuation in truly random manner makes the password too hard to remember. Certainly add the obvious punctuation, but recognize that it doesn’t strengthen your password as much as it might appear.

What we’ve learned from this example

At every stage in working though this example, we made some real improvements. Remember that we are not trying to reach perfection here; we are looking instead to create better master passwords that remain usable. Do not create trouble for yourself by picking a master password that is too difficult to type or too hard to remember.

But we have also learned that human behavior really isn’t very random. The schemes we come up with can be coded into password cracking systems. A good master password is not just limited by what a human can remember, but it is also limited by what a human can create. We can get digits and punctuation into passwords easily enough, but our selection methods involve a lot of predictability. Human behavior is more predictable than we like to imagine. That predictability can be exploited in password guessing programs.

Roll the dice to avoid predictability

dice

If people are so predictable, how can we create memorable passwords that aren’t predictable? It turns out that Arnold Reinhold published a solution to this back in 1995 to help people create strong and memorable pass phrases for PGP. It’s called Diceware.

Because words have meaning, we can remember a sequence of words even if it doesn’t create a meaningful statement. And because there are many more words than there are individual characters, selecting a random sequence of five or so words provides a hard to crack password.

Reinhold produced a list of 7776 short words or sequences (that is 65 for people who care about such things). A word can be selected from the list by rolling five dice (or rolling one die 5 times). Here is a small excerpt from the English Diceware Word List.

  35443  knew
  35444  knick
  35445  knife
  35446  knit
  35451  knob
  35452  knock

If you roll your dice and get the sequence 3 – 5 – 4 – 5 – 1, then your Diceword would be “knob”. Another five rolls of the dice will get your next word. If you rolled 3 – 2 – 6 – 5 – 6 then your next word would be “hike”.

The great thing about Diceware is that we know exactly how secure it is even assuming that the attacker knows the system used. The security comes from the genuine randomness of rolling the dice.  Using four or five words should be sufficient against the plausible attacks over the next few years given observed speed of password crackers. [Updated October 2, 2013]

For those who really want to use this system and get the most security out of it, you should combine Diceware with your own private system. Create a short random password, including digits and symbols and use that in place of one of the dicewords in your final password. So going back to my dogs, Molly and Patty, I might create a weak password like 2dM&P, and suppose my rolls of the dice gets me cleft cam synod lacy, I could then create a master password like cleft 2dM&P cam synod lacy, which would be a very good master password. With repetition, it is something that you can learn to type quickly.

In Conclusion

I would like to remind you of some crucial points I made near the top:

  • We are working toward better passwords, not perfect ones. You should take only as much advice from this as you are comfortable with and no more. Remembering and typing in your master password should not become a chore.
  • If you do change your master password, practice with it regularly so that you don’t forget it. Don’t be afraid to write it down on a piece of paper for a while if you keep it in a safe place.
  • The kinds of master passwords that you need depend on who may try to break it. Even though a typical criminal may have access to sophisticated cracking tools, it is unlikely that they will dedicate hours – much less days, weeks, years or decades – to your particular data.

Related (later) articles

  • This article was followed up by a geek edition which discussed an XKCD comic and some of the mathematical concepts behind this.
  • Once the password cracking tool, John the Ripper, was adapted for taking a shot at 1Password Master Passwords, we looked at how well 1Password with these sorts of Master Passwords hold up
  • In April 2013, hashcat achieved remarkable speeds (300,000 guesses per second) against the 1Password 3 data format, suggesting that a password of 4 or 5 diceware words should be used with 1Password 3.

Dropbox security revisited: Plus ça change

Plus ça change, plus c’est même chose
— Jean-Baptiste Alphonse Karr

Summary: Dropbox remains safe for 1Password use despite some high profile discussion of its security.

Keeping up with news about security issues can make your head spin. It certainly does that to me. Most often important news gets little public attention, and at other times non-events go viral. I think the latter has happened with respect to the complaint filed against Dropbox (PDF) with the United States Federal Trade Commission.

Naturally, when I heard that the complaint had been filed I had to read it closely. After all, the security of Dropbox is of great concern to us all. So what did I find? I found that every security issue mentioned in the FTC filing was something that we had already looked at. I discussed all of these points in earlier posting.

There is no new information in the FTC filing or discussion surrounding it, and so the conclusion posted earlier still stands:

[T]here is no need to panic about Dropbox security. The issues that have come up all do raise very 1Password in Dropbox
legitimate concerns about how Dropbox presents their security claims and addresses issues when they arise, but the actual issues are not nearly as serious as some of the the discussion would suggest. They are even less of an issue for 1Password users. Your sensitive information in your 1Password data is extremely well encrypted and we remain comfortable recommending syncing with Dropbox.

It seems that not even I can resist blogging about the FTC filing, but recent news has put me in the position of having to say that just because there is new “news” doesn’t mean there is new information. Real security must be based on level headed assessments of the threats, whether those are highly publicized or – as is more common – are only discussed by those in the field.

Informed users are the best users

Informed users are the best users, and the outpouring of questions to us regarding Dropbox let us know that you want to be informed. I am delighted by this, but it has also meant that we haven’t been able to respond to queries as quickly as we would like. We are all working hard to catch up, and we should soon be back to providing the speedy responses you deserve and have come to expect from us.