[Reader-list] Hotmail: Why Free Email Might Not Be Such a Hot Idea

Jeebesh Bagchi jeebesh at sarai.net
Wed Dec 12 16:32:29 IST 2001


Hotmail: Why Free Email Might Not Be Such a Hot Idea
Michael Barrett
September 12, 2001

Microsoft is under scrutiny for problems they have in all areas of computers. 
I chose to focus on Hotmail which is a single aspect of the Microsoft empire 
and probably the most widely recognized component. I believe due to the 
nature of email being accessed by almost all users of the Internet, security 
problems with these systems impact the biggest group of people who have on 
average the least amount of security savvy on the Net.

Millions of people, including me, use free email services on the web, 
probably the most popular is Hotmail. Microsoft purchased the Hotmail system 
in 1997 for $400 Million dollars, at the time with a subscriber list of 
around 9 Million accounts. Since Microsoft has taken over the systems they 
have seen tremendous growth, to date Microsoft claims 110 Million 
subscribers. As the system grew, Microsoft began migrating functions off the 
primarily Unix and FreeBSD based systems to Windows platforms to "do a better 
job" handling all the new traffic on the site. This is where some believe 
Microsoft's troubles really began. Many people are of the opinion that the 
Windows operating system is not as secure as other operating systems. I 
believe that the problem lies not with the operating system but how it is 
configured and maintained. The Windows platform can be made secure by 
providing the proper maintenance such as patches, hot fixes and upgrades 
necessary to repair problems all programs have, regardless of platform.

Many people have a bone to pick with Microsoft and what a better way of 
getting back at them than causing problems with a highly visible site like 

As early as 1998 people started making trouble for Hotmail. A Canadian Web 
developer (Tom Cervanka) reported an insecurity in Hotmail that would allow a 
cracker access to a user's password by spoofing the user into re-entering 
their username and password into a crafted MacroMedia Shockwave attachment 
that appeared to be the normal login screen presented by Hotmail. If the user 
re-entered his credentials they would be emailed directly to the cracker. 
This type of trick follows similar exploits using JavaScript to fool the user 
into re-entering their credentials. Microsoft made attempts to protect 
against these types of attacks but did not go far enough, because browsers 
default security configuration are typically wide open and can leave them 
susceptible to these attacks.Browser security settings are one of the key 
factors in a user's ability to guard against such an attack.If more people 
would use the correct settings to (at the least prompt) the user when other 
types of code try to run on their machines, i.e. JavaScript or ActiveX, less 
of these types of attacks would be successful.

Cookies are for more than just eating.

In March 1999, Microsoft attempts to plug security holes in the Hotmail 
systems by mandating the use of Cookies. Cookies are a general mechanism 
which server side connections, such as CGI scripts, can use to both store and 
retrieve information on the client side of the connection. The addition of a 
simple, persistent, client-side state significantly extends the capabilities 
of Web-based client/server applications as opposed to using the IP address of 
the user. According to a Chicago software engineer, malicious users can dig 
URL's out of users' history files and swap out information to gain access to 
other user accounts as long as they are logged onto the system. Privacy 
advocates criticize the Cookie concept as it stores information about users 
that could fall into the wrong hands. Users have many options for the use of 
cookies and all too often fail to utilize the most secure method.Cookies can 
be viewed as fingerprints left behind all over the Internet and users need to 
make themselves aware of what they could be leaving behind. In the security 
field, paranoia is your friend. If you think something you are doing on the 
Net could be turned against you, odds are someone has or will find a way to 
exploit it.I would like to stress again that the users as well as the 
manufacturers, are critical in the security role of the Web.

Microsoft patches problem?? Account still available without password.

In late August 1999 Microsoft claimed to have patched their systems problems 
that allowed people to access accounts without a password, but testing proves 
otherwise. After Microsoft was alerted that two of their servers (one in the 
UK and another in Sweden) were allowing access without a password, they 
brought the sites down and repaired the problem. According to Microsoft there 
was a second security problem, which was blamed on hackers. Apparently a 
programmer published an application that stored login ID and an old login 
script on the affected servers. Some analysts point the problem at the recent 
updates done on Hotmail servers as part of the Passport launch. Passport is a 
Microsoft initiative aimed at bringing all user ID's and passwords together 
making it easier to access the Web and purchase goods and services.Many times 
application problems like this can be directly linked to a failure to follow 
documented policies, or in the worst case no policy at all. A very large 
percentage of security issues stem from known vulnerabilities and flaws. Very 
often these problems are overlooked or put aside due to the tremendous 
pressures on IT staffs to keep production servers online and on schedule.

Audit of Hotmail systems not to be made private.

In late 1999, Microsoft commissioned an outside audit of the Hotmail system 
to verify the fixes put in place after a vulnerability was discovered that 
allowed anyone access to users accounts by simply knowing their email 
address. Microsoft and the Web privacy program, Truste, claim this is a step 
towards improving privacy. Junkbusters, a privacy-protection group, sent a 
request to Microsoft and the Federal Trade Commission for the details of the 
report.Microsoft however refused to make public the findings of the audit 
claiming they were prohibited by the American Institute of Certified Public 
Accountants (AICPA) from revealing the details of the report.The Truste seal 
is intended to protect information on the Web and investigate complaints, 
which is what happened in the Microsoft cause. Since Truste only suggested 
the audit, it seems Microsoft slipped through a loophole, which allowed the 
investigation to remain private. "The big difference to keep in mind here is 
that we never got to the stage where we mandated Microsoft to do the audit. 
If that had been the case, then we might be in a different situation. We hope 
it can be made public," said Truste spokesman David Steer. The privacy 
advocates insisted that Microsoft and the accounting firms disclose the 
details of their finding and it's opinion no later that a week after its 
delivery to Hotmail. I happen to believe that it is not appropriate to 
disclose the outcome of the audit, since the audit was voluntary and made to 
verify the corrective actions Microsoft performed to repair issues they have 
already acknowledged.Companies should feel safe in knowing that audits done 
on their systems are for their eyes only and used to protect themselves. I 
believe that full disclosure gives too much information to those who would 
have otherwise not had such easy access to the information. 

Merry Christmas Microsoft, Linux programmer gives the gift of registration to 

In an embarrassing chain of events around Christmas 1999, Microsoft failed to 
pay the $35.00 registration fee for the Passport.com domain name. This minor 
oversight on Microsoft's part resulted in an outage of the Hotmail system. A 
good Samaritan from the Linux community used his own credit card to pay the 
fee and Hotmail was back on line. Hotmail staff estimated that half of the 52 
million users were affected by the outage. Passport.com is the authentication 
mechanism for Hotmail users which verifies the login and password 
attempts.Users who had already logged in when the domain expired were not 
affected, as were some users who were able to authenticate through another 
system through a process known as caching. While this problem really didn't 
pose a true security risk to the Hotmail system, it speaks to the enormous 
amount of work it takes to run such a system and how something as small as 
paying a bill can have dramatic effects on such a system.

Email like it's 2099.

New Year's Day 2000, Microsoft was bitten by the Y2K bug in the Hotmail 
system. Users who posted messages before November 1999 display a creation 
date of 2099. Microsoft took its time fixing the bug, as it was only cosmetic 
and chose to focus its resources on other more dangerous problems with 
Hotmail.Microsoft was fortunate that the problem they encountered was so 
minor. If a Y2K bug were to have been overlooked in other parts of the 
systems this could have had a much more dramatic effect on the system.

Bulgarian programmer reports yet another security flaw in Hotmail.

According to Georgi Guniski a Bulgarian programmer (who is interestingly 
referred to as a hacker in another article), a flaw in the filtering of 
JavaScript would allow users to be tricked into entering their credential to 
a fake login screen. Using JavaScript commands through an HTML tag in an 
email message could circumnavigate Microsoft's attempts to filter malicious 
code, leaving their users susceptible to trick attacks. Guninski demonstrated 
through the use of obscure and defunct images tags that he could circumvent 
filtering methods put in place. Guninski proved that the tags LOWSRC and 
DYNSRC, which were originally intended to increase the usability of browsers, 
could be used to attack a user due to the nature of the tags.Issues like this 
must leave people wondering how many more "hidden" features/flaws can be out 
there waiting to be discovered. Microsoft claimed to have no evidence that 
suggested the flaw affected any Hotmail users.I believe this problem 
demonstrates how far reaching security problems can be. It is hard enough to 
protect your systems from well-known methods of attacks, but when people 
start using defunct or hidden features it makes this task even more 

Hackers Unite claim to discover "backdoor" in Hotmail systems.

A previously unknown group of hackers reported in late August of 1999 that 
they had discovered a hole in Hotmail security. Through the use of several 
Web addresses a user's login name was the only input required to access other 
user accounts.Access to these accounts varied from viewing message titles to 
full access including forwarding and sending emails assuming the identity of 
the other user. Microsoft denied the existence of a "backdoor" in Hotmail 
systems, and called the problem an unknown security issue.After learning of 
the problem at 2 a.m. PST Microsoft engineers were able to generate the 
initial fix by 10 a.m. and fix a variant of the same problem by noon.They 
then began the difficult task of propagating the fix to all the Hotmail 
servers. Chances are this problem may have been known to Hotmail staff before 
the incident occurred, or not, and an independent security audit may have 
uncovered the flaw before hackers where able to exploit it. Often companies 
fail to get an outside or impartial view of their security until it's too 
late. Periodic internal and external audits can only lead to a more stable 
and secure system.

Please pass the Cookies.

In May of 2000, Microsoft patched a security hole, which allowed intruders to 
break into a user's email account by sending an unwary user an attachment of 
an HTML file. When the targeted user views the HTML file, their Cookies were 
intercepted and sent to a hostile site.Once the intruded has acquired the 
users Cookies they can be used to access the users account. An 
"anti-censorship" site offered the HTML file for download with instructions 
for usage. The site also offered suggestions for Microsoft and users to more 
safely use email by filtering JavaScript attachments, and also prompting 
users about the unsafe nature of some types of documents.Microsoft quickly 
repaired the problem and the exploit was shortly outdated. The problem here 
falls on the shoulders of the users and Microsoft. Far too many users use the 
Internet in unsafe ways and fail to understand their role in security.

How safe are your email attachments?

Late July 2001 left Hotmail users susceptible to the Sir Cam worm.Hotmail 
users benefit from the added feature of McAfee virus scanning on all 
attachments sent through the system. Unfortunately this can lead to a false 
sense of security on the part of some less educated (or trusting) 
users.Microsoft was left open to the Sir Cam worm due to the outdated nature 
of the virus definition files. At the time the bug was known for nine days 
and Microsoft had not yet applied the update to protect its users. Users 
should be aware that everyone shares the responsibility of security and they 
should not rely on one source to check for malicious applications. A virus 
scanner on all user machines is necessary. Above all, unsafe behavior is 
responsible for many of the problems in today's Internet community. If users 
would invoke more common sense when using their computers many of the 
problems with viruses we see today would not be as bad. All users should use 
the simple rules when handling email: Do I know this person? Am I sure this 
email came from the person? Was I expecting an email/attachment from this 
person? Did I scan the attachment before opening? These steps often elude 
people that are either too lazy or too careless to exercise their own common 

Root-Core publishes a new Hotmail flaw.

In August of 2001, the hacker and security site, Root-Core, publicized a 
vulnerability, which allowed others to view private emails. Microsoft said 
the problem existed, but it was a mathematical improbability to utilize. The 
exploit involves customizing a URL based off an existing URL obtained by 
legitimate access to Hotmail.Hotmail uses a "predictable" sequence in their 
mail numbering system, which is based on the UNIX time stamp and an 
additional two-digit number. A hacker could replace these numbers in a 
malformed URL to gain access to other's mail.Microsoft points out that it may 
take thousands or hundreds of thousands of guesses in order to trick the 
system, which may be interrupted by Hotmail's security systems. Root-Core 
used computers to automate the task of guessing numbers and posted the tool 
on their web site. The vulnerability brought unwelcome attention to 
Microsoft's increasing reliance on the Passport authentication systems and 
the integration into their newest release Windows XP. On a side note the 
vulnerability also points out that Microsoft has not yet weanedthemselves off 
of UNIX systems completely, leaving some speculation over the migration of 
Hotmail from an open-source system to strictly Windows 2000 based environment.

Have hacks will travel.

Some hackers have even offered their services to gain access to user 
accounts. A hacker calling himself The Hunter offered a service on anInternet 
forum site to crack any Hotmail or Yahoo user account.The Hunter claims to 
have a system that will always work to discover user credentials. He sells 
his service for $50.00 and offers proof by sending an email from the victim's 
account to the person wanting the information.

I was also able to find programs intended to break the password by "brute 
force" the application could be purchased for$14.95 and claims to hack 
passwords for sites using HTML (like porn sites).It also claims to work on 
FTP, HTTP and POP3. The advertiser points out that the software is illegal to 
use on other and is intended for "reverse engineering" purposes. They also 
chose to list a disclaimer that states it could cause servers to crash and 
that the user was responsible for any damages.

While there will always be dishonest people in the world offering to do 
dishonest and illegal things the focus should be on how we use technology and 
how we can use it safely. Anyone using the Internet should be aware that the 
information they are sharing travels over many devices, all of which have the 
potential to be compromised.People should do all they can to protect 
themselves from prying eyes.

Some users complain they are treated like children.

Dave Miller has had quite a few problems with Hotmail since he started using 
it in 1995. His most frustrating problem is Microsoft treating him like a 
child, literally.Dave made a mistake when setting up an account for his 
daughter and accidentally configured his Passport to be a child's account by 
entering his daughter's birthday. He has made several attempts to rectify the 
problem but Microsoft support claims there is nothing they can do. Once he 
was made a child, his account cannot be changed to that of an adult's. No 
real explanation of why this could be was supplied, except to say that Dave 
should continue to use the process of giving himself permissions through 
another parent account.Although this problem seems minor, one must keep in 
mind that it relates to the Passport system Microsoft has put heavy faith 
into and uses as part of the Windows XP operating system and it's .NET 
initiative.If Microsoft is unable to rectify a simple problem such as this, 
how do they hope to handle the inevitable problems that will come up as they 
grow the use of the Passport system?

Closing thoughts and suggestions.

In my opinion there is no such thing as a 100% secure system, and there never 
will be. As long as there are curious people out there we will continue to 
find flaws and quirks in computer systems. The best way to approach the 
Internet or for that matter any situation is to treat it as a threat and 
educate yourself sufficiently to protect yourself.Common sense is always the 
first and foremost way to protect yourself. Experts have been telling us for 
years and years, don't open emails, attachments, etc. from people we don't 
know or are not expecting things from. Use virus scanning software and update 
signature files regularly. Paranoia and fear are your friends. If something 
doesn't seem to make sense it probably doesn't. Erring on the side of caution 
rarely causes more problems than taking a chance on the unknown.

Information is readily available on manufacturers site and information sites 
all around the Internet. Most people who are victims are a result of outdated 
software or practices.If you are using the Internet in a corporate 
environment your company most likely has guidelines on safely using the Net 
and acceptable use of it.Read and follow these guidelines and you will most 
likely be in pretty good shape.

A few words on Microsoft and Hotmail.I have and will continue to use Hotmail 
and related applications provided by Microsoft.I do always keep one important 
thought in mind, which is to never write or chat anything you wouldn't want 
anyone else to see, because chances are the information could fall into the 
wrong hands.Hotmail is a convenient, easily accessible tool I have used all 
around the world. If used cautiously it's a great way to keep in touch.Users 
of Internet based email systems (or any mail system for that matter) must 
always keep in mind that the information they are sending could fall into the 
wrong hands. Encryption techniques are available for free or at low cost for 
those documents that need to be sent over the Net that must remain private.


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