I just did this upgrade with the kit from eBay, parts from Amazon and my Iphone. I didn't see anyone post directions for that method all in one spot so I thought I would. The pictures from OP were great and very helpful so this is really just the changes when using an Iphone and JScan.
1. I ordered the OEM Kit from eBay:
Here is the one I bought for $139.95
2. I ordered this OBD controller:
Veepeak Mini WiFi OBD2 Scanner for iOS and Android for $16.99
3. I also ordered this cable:
sportuli Fit for Chrysler -12+8 Cable Adaptor for Autel MaxiSys MS908 MS906S 908S MS905 for $35.99
4. Install the Kit from Ebay - this came with instructions.
5. Plug the bypass cable into the two connectors and add the OBD controller on the end.
6. Without foot on brake push the run button on the truck 2x to get it to "run" without the engine on.
7. In your phone settings connect to the wifi that the Veepeak OBD unit puts out. (If you want to also use the internet while connected see below instructions found on Amazon page)
7. Open JScan. (I'll assume you've already purchased the license for your VIN but if not do that now or later when you get to your car settings).
8. Select "Ram DS 1500" on the initial screen almost all the way at the bottom. (There is no option on this software for the DT)
9. Select your OBD tool
10. Toward the top select menu for "ADAPTATION"
11. Navigate to "Trailer Settings"
12. Navigate to "ITBM/HWM Integrated Trailer Brake Module On/Off"
13. Change setting to "Active" and click "GO".
14. Wait for Success.
15. Done - Remove the cable and put the plugs back into the module under the dash.
16. Turn off the truck and turn back on. Test.
Instructions for Veepeak and internet at the same time: go into Settings on your iPhone. Click on the WiFi settings and then tap the "WIFI-OBDII" wireless network (the one created by the Veepeak device.) Click on the "i" with a circle around it to get to the detail settings for the device. In "IP Address" enter 192.168.0.150. For "Subnet Mask" enter 255.255.255.0. For "Router" enter 192.168.0.10. Now your iPhone will use those settings to talk to the Veepeak unit while still having 3G/4G data available for Pandora, iHeartRadio, surfing the web, etc
Total Cost:
Brake Controller Kit: $139.95
OBD Controller: $16.99
Bypass Cable: $35.99
JScan OBD Software 1 VIN license: $18.99
Total Cost: $211.92 (+Tax not shown) installed. The cost for the equipment/software to flash the truck was $71.97. My local dealer wanted $65.00 to do that part and he was on the lower end as I called around. Plus, I don't have to rely on the dealer for any other changes I want to make in the future.