This was my second tasting of Garrison Brothers Ranch Reserve Oloroso Sherry Cask Finished Bourbon. During a review, when a whiskey gives me a particularly strong first impression, positive or negative, I like to give it some time to open up and revisit it. It gives the whiskey a fair opportunity to develop in the bottle while also allowing me to make sure my palate was on target during that first tasting.

Unfortunately, many of the characteristics that concerned me the first time were still present on the second pour.
Nose
The nose is initially dominated by heavy barrel char and bitter oak, accompanied by scorched or burnt sugar. Figs and sour bread dough emerge underneath the char, along with molasses and just a touch of cinnamon. There are some interesting aromas buried here, particularly the fig and molasses, but the char is so assertive that it overwhelms much of what the Oloroso Sherry finish is trying to contribute.
Palate
The first sip brings a very sharp and unpleasant burnt quality accompanied by a noticeable sour note. At 110 proof, it actually drinks hotter than its stated proof, with bitter wood and walnut immediately coming forward.
As you continue sipping, some enjoyable molasses and Sherry notes begin fighting their way through the heavily charred bourbon. Honey, fig, and a little sweetness gradually emerge. The good news is that the bitter, burnt quality diminishes somewhat as the palate adjusts and the whiskey opens in the glass. The bad news is that it never diminishes enough.
The Oloroso Sherry finish tries to impart some welcome sweetness and dried-fruit character, but it has a difficult time overcoming what, in my opinion, tastes like an overly charred underlying bourbon. Instead of the Sherry and bourbon working together, I find myself searching through the char and bitterness to get to the more enjoyable flavors underneath.
Finish
The finish largely continues what preceded it: burnt and bitter wood accompanied by dried fruit, lingering oak, and some residual Sherry sweetness. There is decent length, but the bitter barrel character once again remains more prominent than I would prefer.
Overall
After a second tasting and giving the whiskey additional time to open up, my impression remains largely unchanged. There are some genuinely enjoyable flavors here. I can find the fig, molasses, honey, dried fruit, and Oloroso Sherry sweetness, and when those notes manage to break through, they provide glimpses of what this whiskey could have been.
For me, however, the underlying barrel influence is simply too aggressive. The bitter oak, burnt sugar, sourness, and heavy char repeatedly overpower the more nuanced characteristics of the Sherry finish. The whiskey does improve somewhat with continued sipping, which is certainly a positive, but it never reaches the point where those harsher characteristics recede enough to create the balance I'm looking for.
Ultimately, the Oloroso Sherry seems to be doing everything it can to soften and enrich the bourbon, but it's fighting an uphill battle against what I perceive as an overly charred whiskey underneath it. There are good flavors trying to get out, I just wish the barrel would get out of their way.