How can I enable breakpoints in both .exe and .dll C++ projects in a single solution?

I have a solution in visual studio with one .exe(exe1) project and 2 dlls (dll1,dll2). .exe depending on these 2 dlls.

when I build dll2 and immediately build exe1, it says dll2.lib is not found. But if I wait for a 5 seconds and build exe its building successfully. I dont understand why

What I want is to debug both dll and exe when I am running the solution with exe as my starting project. But since I am building exe at the end , only exe break points are enabled (A different version of symbol is loaded for dll1. dll2 has no such issue); Now if I build dll1 and directly run the code I can only put break points in dll's code ; exe break points are hollow and not hit.

How can I achieve debugging both exe and dll. dll2 has breakpoints that are hit. whcih settings I should check in dll1?

Output directory of all these are same folder.

I have read this How to debug an exe with multiple dlls using breakpoints But I am not able to manually add symbols to the file too. It says matching symbol file not found when I am selecting the pdb file

Thanks all, The target name of .exe was set as the name as dll in .exe's project settings, and was not set for exe so by default it was also taking the same name effectively both producing same pbd files