The Milano cookie has always been something of an enigma for me. With its elegant yet simple design and name conjuring images of the Italian Alps, it was beyond my childhood capacity of appreciation. Later in life, after I had graduated from a packaged cookie diet consisting entirely of Oreos and Chips Ahoy, Milanos still perplexed me. A dense yet slightly chewy crumb and buttery but dark chocolate flavor pointed toward a cookie on its own plane, distinct and unabashedly unique from every other prepackaged treat.

Oh yes, and terribly delicious.

It goes without saying that we expect much from Milano cookies. When you nail the chocolate flavor better than 95 percent of the competitors, I think expectations are a given. Nevertheless I couldn’t help but wonder if that sophisticated edge would translate with the addition of pumpkin spice. It’s one thing to pair mint and raspberry with chocolate, but when you start playing matchmaker with chocolate and the sometimes ambiguous concoction of fall spices, the results aren’t always so endearing.

Examining the bag confirmed my initial skepticism, as there’s no mention of pumpkin or the usual suspects of cinnamon or brown sugar in the ingredients. Nevertheless the orange lip representing pumpkin appeared on each cookie, while an unmistakably pumpkiny aroma danced from the open bag in perfect step with aromas of shortbread and chocolate.

It’s really a scintillating aroma, one with notes of pumpkin ice cream and pumpkin loaf cake supporting the dance. Actually, it’s so great I nearly passed out of asphyxiation due to a prolonged moment of sticking my schnoz right into the bag and failing to breath anything but the glorious smell of autumn.

The orange “cream”—for want of a better word—is thin and slightly viscous, with a texture somewhere between cream cheese on a hot day and the filling they stick inside those stacked wafer cookies. Tasting it from the lip of the cookie, it comes across as a less intense version of Philadelphia Pumpkin Spice Cream Cheese, right on down to a slightly artificial flavor that seems a bit too quiet for fall’s most iconic squash.

Artificial flavor aside, there’s a pleasantly light sweetness and lickable texture that leaves me wanting more. The problem is there really isn’t much more to be had. Even though the chocolate-to-pumpkin filling ratio is about 1:1, the pumpkin finishes a distant third in its impact. The filling and the spice together are enough to let you know we’re talking pumpkin and not just cinnamon-flavored cookies, but the milk chocolate filling and scrumptious cookie base seem unwilling to let the pumpkin intrude on their synergy.

It’s been my experience through a quarter century of pumpkin eating that pumpkin is a very jealous flavor. It just doesn’t like playing second fiddle, much less third string. Yet in the distinct and careful balance of buttery cookie crumb and rich chocolate taste the pumpkin seems an awkward third wheel, attractive enough to want on its own, but not enough for either of the other two elements of the cookie to commit to.

It’s as if the cookie and the chocolate know what they have together, and while tempted by the pumpkin’s autumnal notes, neither flavor wants to commit to the newcomer over its tried and true other half. My God, it now occurs to me as I polish off another cookie, I have just described a twisted escapade of cookie love.

The sophisticated chocolate taste and buttery crumb native to all Milanos make the Pumpkin Spice Milano flavor unique and tasty. Yet for such a trendsetting cookie the pumpkin spice flavor doesn’t come through enough to make it a distinctively pumpkin product, while the hints of an attractive and creamy texture mitigate it to an awkward role player. As for that role, it’s just not cast right, and despite a promising beginning and intoxicating aroma, the Pumpkin Spice Milanos failed to make me fall in love with their take on the seasonal flavor.

(Nutrition Facts – 2 cookies – 130 calories, 60 calories from fat, 7 grams of fat, 4 grams of saturated fat, 0 grams of trans fat, less than 5 milligrams of cholesterol, 40 milligrams of sodium, 16 grams of carbohydrates, less than 1 gram of dietary fiber, 10 grams of sugar, and 1 gram of protein.)

Item: Pepperidge Farm Pumpkin Spice Milano Cookies
Purchased Price: $2.50
Size: 7 ounces
Purchased at: Safeway
Rating: 5 out of 10
Pros: Quite possibly one of the most enjoyable smelling cookies in creation. Buttery Milano cookie. Rich milk chocolate flavor. Pumpkin flavored “cream” is slightly reminiscent of pumpkin cream cheese. That feeling you get when you buy Milanos.
Cons: Too little pumpkin filling. Slightly artificial pumpkin spice “cream.” Third wheel flavors. Death by cookie bag. Nineteenth century packaging of Milano cookies.