Fill a pot with enough oil to fry the churros (about 3 inches high) and pre heat it to 360 degrees Fahrenheit. I use a Taylor Precision candy thermometer for this.
In a small saucepan: mix together water, oil, sugar, and salt. Bring to a boil then turn off the heat when the sugar is fully dissolved. Let it cool for 1 minute.
Add the vanilla extract and mix.
Add the flour and mix until just combined- no more than 20 seconds. Do not over mix! It's okay if you can still see some dry spots of flour.
Let the dough cool for 3-4 minutes. This step is important for the right consistency. It will be much easier to pipe out of the bag. Place the 1M Wilton star tip into a heavy duty piping bag (do NOT use disposable or Ziploc bags!), then stuff with the dough. You should be able to squeeze the dough out using a little pressure with one hand.
When the oil reaches 360 degrees fahrenheit, pipe in 4 to 5 churros at a time, cutting them with scissors at about 5 inches in length. Do not overcrowd the pot or the oil will drop in temperature too much. You want it to stay between 350-360 degrees. From this point on, the following steps will need to be done in batches.
Flip the churros over after a minute for even browning. Keep an eye on the thermometer and make any adjustments to the heat source if needed. The churros should be done after about 3-4 minutes. If you like them extra crunchy, let them fry a little longer until they are a deep golden brown.
Shake off excess oil (be careful) and let the churros rest on a cooling rack for 1 minute. Do not roll in sugar right away- this will cause the sugar to clump too much and won't stick well to the rest of the churros.
Roll the churros in the sugar/cinnamon mixture until well coated. Repeat the frying process until all the churros are done.
To make the chocolate coffee dip:
Heat the heavy cream, instant coffee packet, and pinch of salt in a small sauce pan on low until dissolved. Do not hard boil- this should just be a simmer.
Turn off the heat and add the dark chocolate. Mix until fully dissolved and keep on low heat until serving (the dip will harden when cooled- it is meant to be served warm and eaten right away).