One thing to check is polarity on the pedals. I'm not sure that boss and Digitech are the same inner/outer polarity, although if they're working at all you're probably OK.
If you're using a single power supply, add up the individual current requirements of the individual pedals and check that number against the max output of the power supply. If you are trying to draw more current than the max available, you will have failures.
Voltage is one thing - mostly 9V for pedals, but some differ. However, the current demand (usually listed in Milliamps) of each pedal varies. Power=voltage times current, and if you try to draw more power than is available, you have problems.
BUT - that doesn't sound like your problem. Yours sounds like a broken wire. If the power supply capacity number checks, maybe you just have a bad wire or connector. To troubleshoot wires, I usually lay things out, connect them and turn them on, and start twisting the wire in my fingers a few inches at a time, starting at the power supply. Most breaks are at one end or the other from flexing the wire too much.
It's always easy to cut a couple of inches off the end of the power supply cable and replace the connector at the pedal end - not as easy to replace the whole wire from the supply to the pedal.