When Upgrading Pier 2 to Pier 3, the files storing pictures were not accessible, this seemed like changes is the hashing, or something similar. On many Smalltalk hosting sites, space is a scarce resource (As of 2014-July, http://seasidehosting.st offers 240Mb, http://www.pharocloud.com provides 3Gb for $2 per month). There are some suggestions for using apache here, if you have the server available. Serving pictures in Smalltalk isn't the most efficient idea. One solution is to server them using Dropbox (this link has an example), this is effective for a small amount of traffic. An example of the tags are:
{{{html: <div style="clear: both">
<img src="https://dl.dropboxusercontent.com/s/pfdwani2bwmus49/CompareWikiEditors.png" alt="Compare wiki editors" />
</div>}}}Note that some companies block dropbox, so it depends on the situation. Using NGinX is an alternative.