Lightroom Photoshop

[#1]

On lightroom I used to be able to send an image to photoshop by hitting the enter key, and once edited I would save it as a jpeg and it would go back beside the raw file in lightroom. However now I have to right click and send to photoshop and when I have edited it I try to save it as a jpeg and it does not go back to lightroom. There could be a majorly simple explanation or something I'm missing so any help would be majorly appreciated please. I've spent three hours faffing about, the ensure jpegs are displayed alongisde raw is selected and I am using a Mac. 

[#2]

On lightroom I used to be able to send an image to photoshop by hitting the enter key, and once edited I would save it as a jpeg and it would go back beside the raw file in lightroom. However now I have to right click and send to photoshop and when I have edited it I try to save it as a jpeg and it does not go back to lightroom. There could be a majorly simple explanation or something I'm missing so any help would be majorly appreciated please. I've spent three hours faffing about, the ensure jpegs are displayed alongisde raw is selected and I am using a Mac. 

[#3]

Which version of the Mac OS?

Which version of Photoshop?

Which version of Lightroom?

When you save the file in PS, are you doing a "save" or "save as"?

What is the LrC sort order of the folder your files are in?

Do you have "stacking" turned on?