When I ate a sleeping dog today, KoLmafia did not notice that I acquired the Dog Tired skill until I manually visited the char sheet. Perhaps the HTML for "You acquire a skill" has changed. Fortunately, I had the debug log going.
Code:
<td valign=center>You acquire a skill: </td><td><img src="http://images.kingdomofloathing.com/itemimages/jarl_regdog.gif" onClick='javascript:poop("desc_skill.php?whichskill=91&self=true","skill", 350, 300)' width=30 height=30></td><td><b><a onClick='javascript:poop("desc_skill.php?whichskill=91&self=true","skill", 350, 300)'>Dog Tired</a></b></td>