Hi, thank you for bring this issue to my attention. I’ve looked at this and have a partial solution but it also looks that there’s a bug in DEVONthink for full support of this.
First of all, it look like opening the document externally from DT indeed doesn’t register in Trickster. My guess is that the approach DT uses to launch an external application may not be registering on the OS level and thus the information doesn’t arrive to Trickster either.
Now, on DEVONthink level itself, you can modify the Smart Rule condition to also fire when “Open Externally” condition is met like in the screenshot below. I tried this but it only seems to work when opening in an external tool using “Open With” in the context menu, not when the document is opened by an external tool by double-clicking on it, when that option is enabled in DT’s preferences, like in your case. This latter behaviour (not running the Smart Rule when double-clicking) I would consider a bug in DEVONthink since I’d expect “On Open Externally” to fire regardless if I double-clicked on a file to open externally or used “Open With”. Please contact DEVONthink’s support about this, if this is important.
It may make sense for me to update the Smart Rule to include “On Open Externally” by default but until this bug is fixed in DT, it will be of limited use.