I’d definitely be working on helping develop the strategy of Adding Up.  Watch this video and skip ahead to 8:30 to me describing that strategy with money, example is larger amounts but would be the same strategy: https://pd.buildmathminds.com/courses/bmm-archive/lessons/vlogs/topic/solving-money-problems-with-subtraction-strategies/ 

Adding up is way easier than subtracting and the ‘adding up’ strategy used to be called “The Cashier’s Algorithm” because it was how cashiers used to count back change to customers.

As for activities to help develop the idea of making change up to a dollar, the #1 activity would be to create a reward system with a ‘store’ the child can purchase items from.  The best way to learn the money system and the act of giving, or getting, change back is to actually do it.  So if you can find ways to have the child earn money (even if it’s fake money) and then they can use that money to buy items from you (a cool eraser, a new pencil, etc) it’s a natural motivator for them to want to learn to do it correctly in order to make sure they are getting the right amount of money back.  A few years ago, one of my best friends did a Virtual Summit session explaining how their whole 4th grade does a reward system where students earn and spend money.  It sounds like you are working one-on-one with this kid?? But you can watch the session here to get ideas: https://pd.buildmathminds.com/courses/2022-virtual-math-summit/lessons/vms22/topic/vms22-ellis/ 

The other activity I’d encourage you to do is “I Wish I Had.”  I’d first do the activity with just numbers and visuals that don’t involve money and then work into doing it with money, starting with small amounts then moving to change up to a dollar.  The idea of the activity is you say (or show) an amount and then say “I wish I had ____. How much more do I need?”  So lets say I show a picture of 7 items in a ten frame, I’d say “I have 7, but I wish I had 10.  How much more do I need?”  Keep doing the activity over time, sometimes even removing the visual to see if they can do it without a visual.   “I have 7 markers, I wish I had 10.  How many more do I need?” but don’t show or give any markers to see if they can do it without visuals.  If they still need visuals, go back to using them.  Then as you see they are able to do I Wish I Had without it being money, then I’d start doing ones with money…but still use visuals.  Example: show 38 cents, “I have 38 cents, I wish I had 50 cents. How much more do I need?”

Hope this helps,

>>>>>Christina