There's a long list of problems here (admittedly from 2002 but the product hasn't really changed since then)
Edit: here's the text from the link, in case it disappears. Page is licensed under CCA3.
Visual SourceSafe: Microsoft's Source Destruction System
by Alan De Smet
There are many fine solutions for revision control systems.
SourceSafe isn't
one of them.
I used SourceSafe for five years though spring 2002 . It has consistently
been an unpleasant experience. New versions failed to improve anything of import.
I hope to dissuade you from using SourceSafe,
sparing you the bad experiences I have had.
Missing Features
SourceSafe lacks usable branching support
A revision control system should provide powerful branching
support. With strong branching support, developers can easily
make minor revisions of old versions while work toward the next
major release continues. Highly experimental code can be checked
into a branch, keeping it separate from mainstream development
but backing it up and making it available to other developers.
If the project is "frozen" while a milestone or final release is
built, a developer can continue development toward the next
version on a branch. (Or more commonly, a new branch can be
created for the freeze while general development continues on the
main branch. When the release is done, changes on the frozen
branch can be merged back into the main branch.) SourceSafe's
branching support fails to effectively support any of this.
With powerful branching, a revision control system must
also provide strong merging support to reconcile different
branches. At the least, the system must allow a developer to
examine the differences between two branches, modify them to
create a merged version, and when satisfied check them in.
SourceSafe's merge support is tightly integrated with checking
in, making it difficult to examine differences and test the
proposed merge before checking it into the tree. With this weak
level of support, it's easy to check non-functioning code into
the revision control system.
SourceSafe cannot be safely extended
It should be possible to easily extend your revision control
system with additional functionality. The ability to send out
emails summarizing check-ins is essential. When working with a
team, regular email messages listing files checked in and the
check in messages associated with them really help keep everyone
up to date with recent changes. You might also want to add
filters to prevent check-ins of code that doesn't meet certain
requirements (standard copyright statements or doesn't compile).
SourceSafe barely supports this. While it is possible, every single
client needs to have the additional functionality installed. If
a single client lacks the extension, it will quietly fail to
behave as expected.
(For details, see
Visual SourceSafe 6.0 Automation.
Check the section "Trapping SourceSafe Events? An Overview".) You can
pay even
more for a third party solution, but does it make sense to
invest more money in a fundamentally broken product?
SourceSafe silently leaves stale files on your local system
When updating your local workspace to match the server, files
which were deleted on the server should brought to your
attention. (Or deleted, since the old version can be retrieved
from the revision control system.) Failure to do so risks out of
date files being used in your project, often causing problems.
I've frequently run into this problem when an out of date header
file is incorrectly included into my project. SourceSafe fails
to delete the out of date file or provide any warning.
SourceSafe badly handles slow networks and the public internet
SourceSafe is unusable over slow network connections. It's
effectively unusable over the public internet. In addition,
because SourceSafe works over network shares, if you place a
SourceSafe server on the internet, you're exposing any weaknesses
in your servers file sharing implementation to the entire world.
Of course, if
you're willing to invest more money in your ineffective revision
control system, you can buy a third party
product to solve this problem.
Managing third party modules is difficult with SourceSafe
It's not uncommon for a developer to use third party modules
in your project to quickly add required functionality. For
example, you might use Codejock Software's Xtreme
Toolkit. It's natural to check these third party modules
into your revision control system. This way, when you step
backward in time to examine a previous revision, you can get the
same versions of supporting libraries and third party modules
that were used to build your code at this time.
Unfortunately, SourceSafe makes tracking a third party module
extremely difficult. Initially checking the first version in
isn't hard. Checking a new version in requires a good memory and
attention to detail. To add a new version, you first recursively
check the folder holding the module out. Now delete the
directory on disk and replace it with the new version. Check in
new version in. You now need to identify any files or
directories added in the new version. Right click on the
module's folder in SourceSafe and use "Show difference" to
recursively generate a list of files which have been added. Note
which directories hold files which have been added and which
directories have been added. Now close the report of differences
(the report is modal, preventing you from using SourceSafe while
visible). Add the new directories as you would normally add
directories. To add the new files, visit each directory holding
new files and use File > Add Files to add them. Again, use the
"Show difference" command to recursively generate a list of files
which have been removed. Note these files and close the the
report of differences again. Now delete each of these files in
SourceSafe.
If you've actually tweaked the third party module, SourceSafe
provides no particular help in tracking down the differences and
merging them into the new version.
(For comparison, to check in a new version of a third party
module using CVS, you would
simply run the command "cvs -q import -m 'Import of Xtreme
Toolkit 1.9' xtremetoolkit Codejock XT_1_9". That's it. If
you've made changes to the module that need to be integrated, you
would use "cvs checkout -j XT_1_8 -j XT_1_9
xtremetoolkit". That will give you a local copy of the
merged changes which you can immediately check in if
satisfactory.))
Viewing and retrieving historical versions is extremely
slow
It's not unusual to need to get a historical version of the
source code. You might need an older version to investigate a
bug report, or the current code is malfunctioning and you need to
get a functioning version. SourceSafe supports this, but it's
extremely slow for non-trivial projects. To get a historical
version, you first need to generate a history for the entire
project you're interested in. On a project with hundreds of
files and just over one year of history, this can easily take
over five minutes (even if you restrict the actual search to the
last 48 hours of changes). Once this history is generated, you
specify the version to get by selecting the last check-in to
accept. The slow speed at which this process is completed
discourages developers from examining previous versions,
defeating much the purpose of a revision control system.
Difficult to maintain multiple local copies of one
project
While making extensive changes to a copy of the project, you
may be asked to make a small change to the project. The most
efficient and safest way to do this is to get another copy of the
project to make the change on. SourceSafe presents two problems
in doing so. First, SourceSafe only recognizes a single copy of
the project on your system. You'll need to either move the
project directories back where SourceSafe expects the canonical
copy, or you'll need to reset SourceSafe's notion of where the
canonical copy exists. Using either technique, it's easy to
accidentally point SourceSafe at the wrong project and check the
wrong versions of files in. Secondly, SourceSafe's weak merging
features mean that if you need to change the same file in both
copies of the project, you'll need to be very careful that
changes to one project don't destroy changes in the other.
Safety
SourceSafe degrades on large projects
Microsoft recommends that your database not exceed 5 GB.
(Source: Microsoft Best Practices)
While this is a large database, it's not unreasonable for a large
project, especially if you check in large binary files (like
Microsoft Word documents).
SourceSafe integration can crash Visual Studio
SourceSafe can hang or crash when your system loses connection
to the SourceSafe database. While this is irritating for Visual
SourceSafe, this can cause you to lose work when Visual Studio is
using SourceSafe integration. Simple having a SourceSafe managed
project open in Visual Studio is enough to open yourself to the
risk. To minimize this risk (and speed up ClassView), I suggest
you
follow
Microsoft's directions on disabling SourceSafe integration.
SourceSafe relies on dangerous file sharing
SourceSafe doesn't really run as a server, but as a set of
files shared over SMB. As a result, you're relying on each
individual client to not misbehave. A single misbehaving
computer can destroy the database. A problem in the file sharing
implementation on your operating system can damage the database. Users only needing read-only
access to the revision control system need write access to the
server, increasing the risk (Required Network Rights for the SourceSafe Directories).
SourceSafe should be scanned for corruption weekly
Of course, with this high risk of corruption,
Microsoft recommends that you run the Analyze diagnostic program
weekly.
(Source: Microsoft Best Practices)
While Analyze is running all of your developers are
locked
out of the system (I hope everyone remembered to quit from
SourceSafe first!). My experience with SourceSafe shows
that a 2 gigabyte system running under Windows 2000 takes several
hours to check if run weekly.
SourceSafe handles multiple time zones badly
If you have teams using the same SourceSafe repository in
different time zones, you're likely to have problems. (See
Microsoft's details on the time zone bug.) The only solutions
Microsoft provides are to incorrectly set the clocks of the
computers to a single time zone, or to purchase a third party
product.
Relatedly, this is a potential problem if any of the client
computers using SourceSafe fail to have synchronized clocks.
Differences of several minutes between computers can cause
strange behavior from SourceSafe with it tries to reconcile
information that appears to come from the future.
SourceSafe becomes corrupted
Your revision control system must be trustworthy. You're
entrusting your hard work to your revision control system. If
your data is corrupted, the system is worthless. SourceSafe's
fundamental design assumes that clients are trustworthy, always
function correctly, and that nothing interferes with the
communication causing corrupted data. As a result, SourceSafe is
fragile and untrustworthy. I have worked with SourceSafe at
three different jobs. In each case, eventually the SourceSafe
database became corrupted. Data has been corrupted, work has
been lost, time has been wasted on the problem. Speaking with
other developers, I have learned that my experiences are not
unique.
Irritations
Minor actions like changing the directory erase the entire
contents of the output window, making it difficult to examine past
actions.
Comparing your local version to the remote repository is
clumsy. You select the directory you're interested in SourceSafe
and select Compare Differences. The resulting report is modal,
preventing you from working with SourceSafe while examining the
report.
When getting the latest version of files from SourceSafe,
each file changed locally causes a dialog to pop up to confirm
the update. The update action entirely stops while the dialog
waits for your response. This is particularly irritating if you
get the latest version, step away from your computer for a while,
then return to discover that SourceSafe is only 10% done and
waiting for your response. You can prevent the dialog from
returning in several ways, but in doing so you get no
indication that any such files were encountered. So when you
return to the finished update, you will have no idea that
SourceSafe encountered potential problems. SourceSafe should
note these files in the output window when encountered, making it
easy to scan the output window for files to be investigated.
Conclusion
If you're considering SourceSafe, consider something else. If
you're using SourceSafe now, migrate away as soon as possible.
Here are just a few.
If you simply must use SourceSafe, definitely take the time to
look at Microsoft's list
of bugs in Visual SourceSafe 6.0 and list
of fixed bugs in Visual SourceSafe 6.0 so you know what to
expect. (These links were originally taken from Microsoft's Bugs page.
This page may be useful if you have a different version of
SourceSafe or the above links fail.)