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I'm sorry, I can't duplicate this problem, but I can share some of the code I've used to try to re-create it. First, I define my image and label like this:

\subsubsection{Post-Conditions}

FOO, and BAR.

\begin{figure}[Ht]
\includegraphics[width=.9\textwidth]{UseCases/MyImage.jpg}
\caption{The description of my image was here.}
\label{label:MyExampleLabel}
\end{figure}
\clearpage

Next, I reference this label from somewhere else in my document like this:

(Figure ~\ref{label:MyExampleLabel} on page ~\pageref{label:MyExampleLabel}) YADA YADA YADA

After I generate my PDF, the references look like this:

(Figure 4.2 on page 39) YADA YADA YADA 

and the label on my image looks like this:

Figure 4.2: The description of the image was here.

These are correct, as this is the second image in this section of my document.

Depending on whether or not I use that \clearpage command, the image either shows up in Section 4.8.5 of my document, or it floats to wherever pdflatex thinks it should go.

I'm sorry I can't reproduce the problem ... thinking, thinking ... I haven't upgraded my pdflatex version in several years, so that could be a difference. I just ran pdflatex --version, and I see this output:

pdfeTeX 3.141592-1.21a-2.2 (Web2C 7.5.4)
kpathsea version 3.5.4

I guess I have the PI version of pdfeTeX. Also, I'm running this on Mac OS X 10.5.x.

One other thing I just thought of: Check your pdflatex log file and see if there are any clues in there.

Oops, one last note: here's the pdflatex message I used to see telling me my references were going to be wrong:

LaTeX Warning: Label(s) may have changed. Rerun to get cross-references right.

Whenever I saw this message I knew I needed to run pdflatex again.