Pineapple Upside Down Cookies and other goings on

I had my first physical since high school last week.  I had horrid flashbacks of sitting in the cafeteria waiting for my number to be called so I could either go pee in a cup, have a nurse prod my stomach to ensure I wasn’t pregnant, and/or get weighed in front of the football team.  At least I wasn’t a dude…they had to cough or something…it was weird, I pleaded with my mother never to attend mass physical day ever again.  And I didn’t, but my brothers had to.  Maybe they are right, mom and dad like me more.

You can imagine I was not exactly looking forward to said physical. But who really does, right?

Overall, it wasn’t painful if you don’t count the blood draw or the TB test.

It was not a complete waste of time if the hour and twenty minutes spent waiting for my kidneys to filter my blood and produce about 1/2 cup of urine doesn’t count.

It was not gross if you don’t consider peeing in a cup gross or the fact that my aim/ability to pee into a cup has not improved since high school.  ( I have a beef with this whole process…peeing in a cup was created for dudes, by dudes.  Not ladies.  Unless I am doing it all wrong.)

It wasn’t awkward if you don’t count the misunderstanding between mumbling male nurse and myself about the state of my bladder fullness, which led to me standing in a drug testing bathroom waiting a respectful amount of time before I reappear and explain that my kidneys had yet to perform.  And yes I blamed my kidneys…

It wasn’t weird if you don’t count the fact that they weighed me after I had drank at least 60 ounces of water or that I had to find my own band-aid for my vein puncture.

I didn’t look too ridiculous if you consider a 28 year old women, wearing a flowered hospital gown and knee high black hose, sitting atop her folded clothes, reading Tina Fey’s book Bossypants in the exam room waiting for the the doc normal.

OK, so overall I think my self respect was knocked down a notch, but I did get a clean bill of health and I was able to read a good amount of my large print version of Bossypants.  (Tip…always look in the large print section of library for newer books…they are nearly always available when the normal book is on hold.  However, this may be like parking in a handicap spot, shrug…)

Why the physical?  Well peeps, I have new and exciting news.  As we ring in the New Year, I will be starting a new job!  Eeeek!  I will still be a pharmacist, but will no longer be practicing in the retail setting.  I am going to the other side and jumping feet first into the world of hospital pharmacy.  I am crazy excited and a little bit nervous, but overall happy as a peach!  I am ready for a new challenge and getting back onto a normal schedule, as I will be coming off nights and going onto days…hooray for sleep!  I will truly miss my fellow night owls, who have become dear friends, however when an opportunity presents itself, you have to jump.  So, I am jumping.  Plus, I think I will be able to spend more time working on this here blog, which pleases me to no end.

But before the new job starts and before we ring in the New Year we must first get to Christmas.  Let us not rush.  I still have one more week to make and write about cookies.  I still have one more week (OK 6 days) to finish my shopping.  I have stll have one more week ( OK 5 days) to get  a birthday present for my dad.  So, let’s begin!

Pineapple upside down cookies.  Like the cake but in cookie form.  You have the cake – which in this case is a soft and fluffy cookie.  You have the crushed pineapple on top – which in this case is scattered throughout the cookie.  You have the brown sugar and butter topping – which in this case is the frosting.  It is all there, minus the weird maraschino cherries that I always omit because I think they are bit strange…nothing should be that red.

Oh and go read Tina Fey’s book Bossypants, it will make you laugh out loud.  Seriously.


Pineapple Upside Down Cookies

Makes about 2 to 3 dozen


  • 3 Cups All Purpose Flour
  • 1/2 teaspoon Baking Soda
  • 1/2 teaspoon Baking Powder
  • 1/4 teaspoon Salt
  • 1 Stick Butter, room temperature
  • 1 Cup light Brown Sugar
  • 2 Eggs
  • 1 teaspoon Vanilla Extract
  • 3/4 Cup Sour Cream
  • 2 Cans ( 20 ounces) Crushed Pineapple, well drained


  • 1 Stick Butter
  • 1 Cup Light Brown Sugar
  • 1/4 Cup Heavy Cream plus a few extra tablespoons to reach desired consistency(or milk or half and half, use what you have)
  • 1 + 3/4 Cup Confectioner’s Sugar

Preheat oven to 350°F.

Sift together dry ingredients ( flour, baking soda, baking powder, and salt).  Set aside.

In a large mixing bowl, blend together (with hand or stand mixer) butter and brown sugar.  Beat in eggs, vanilla, and sour cream.   Add the well drained crushed pineapple and mix well.  Remember to scrape down sides and bottom of bowl, ensuring even mixing.

With mixer on low, slowly add the dry ingredients and mix until all the flour has been incorporated.

Scoop dough out onto parchment lined cookie sheets about 2 inches apart (they will spread slightly).  Bake in preheated oven for about 12 minutes.  Remove from oven and transfer to cooling rack. Ice cookies once they are completely cool.


In a small saucepan over medium heat, melt the stick of butter.  Once the stick of butter has melted stir in the brown sugar and stir to dissolve.  Bring mixture to boil and then reduce heat to medium low and continue to boil for 2 minutes.  Once the two minutes are up, stir in the  cream and return to boil, stirring constantly.  Once it reaches a boil, remove from heat and let cool.

Once the mixture is at least lukewarm, transfer it to a mixing bowl and with beaters on low, slowly add the confectioners sugar and beat to desired consistency.  You may want to add extra cream/milk to icing to make it thinner  – I did.

Tip:  I made my icing the night before and stuck it in the fridge, the next morning it was rock hard!  I stuck it in the microwave for one minute to loosen it up, stuck it back in the mixing bowl and slowly added more cream (little by little) until I reached the desired consistency.  The thinner the icing the easier it is to ice the cookies.

The icing will thicken/harden the longer it sits, so ice the cookies as soon as the icing is ready to go




Published by Mallory

A twenty - something (at least for a little while longer) trying to squeeze the most out of life...but mainly baking/cooking up a storm in my kitchen while watching Netflix.

11 thoughts on “Pineapple Upside Down Cookies and other goings on

  1. This looks fantastic, I have been a bit baked-out from the holidays but this has reinspired me. Maybe not for a group though, just me! 😉


  2. I seaerched for pineapple cookies on google and I just made these with my sister and they are in the oven now! I am not going to freeze them because we are having guests over tonight. they smell good but m=when I tasted the batter it was tangy…. i hope it wontt be when they are finished. Very easy though! thank you!


  3. I found this recipe on Pinterest and had to try it!! I just finished frosting them! I thought something was off when I finished the batter – it seemed too runny, more like a cake batter than a dough. I baked them off anyway, without any changes. They rose very little and are pretty chewy – like not enough dough for all the pineapple, maybe? I followed the directions and measurements. The only difference I could think of is that my stick of butter was more like ‘softened’ than ‘room temp.’ Do you think that would make much of a difference? Any suggestions?

    Ps. The frosting is TO DIE FOR! I’d swim in it if I could!


  4. I made these cookies last night and I think they were a flop. The consistency after baking is chewable rubber and no taste of pineapple. Any suggestions of what could be wrong? P.S the icing was the best part


    1. Possibly over-mixing? You will want to mix just until the flour is incorporated otherwise that gluten starts to act up. Or too much juice still remained in the pineapple? I am sorry these didn’t work out for you!


  5. I made these tonight,and don’t think I’ve ever made such a flop of a cookie. I followed all the instructions & double checked the ingredients.
    I would advise anyone else wanting to try these to steer clear–a waste of time and money!!! They’re not even sweet enough!!! Rose


    1. Rose, I am so sorry for your frustration with these cookies. It has been awhile since I have made these but I am going to whip them up again this weekend and figure out the problems. I test recipes 2-3 times before I post them to weed out any problems. I will let you know if I find anything askew with the recipe. I know how frustrating it is to have a recipe fail and your time and money is valuable and I apologize for any problems.


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