CCS/TMS320F28377S: Compiling dss files into a .jar file

I have specified a manifest file with the following command.

jar -cvfm flasher.jar manifest.txt flasher.class

my manifest.txt looks like this:

Main-Class: flasher.class
Class-Path: . /Applications/ti/ccsv6/ccs_base/DebugServer/packages/ti/dss/java/dss.jar /Applications/ti/ccsv6/ccs_base/DebugServer/packages/ti/dss/java

When I run the generated .jar file I get the following error:

flasher(master) > java -jar flasher.jar
Error: Could not find or load main class flasher.class

Looking at the created manifest I see the following:

flasher(master) > unzip -p flasher.jar META-INF/MANIFEST.MF
Manifest-Version: 1.0
Class-Path: . /Applications/ti/ccsv6/ccs_base/DebugServer/packages/ti/
 dss/java/dss.jar /Applications/ti/ccsv6/ccs_base/DebugServer/packages
 /ti/dss/java
Created-By: 1.8.0_111 (Oracle Corporation)
Main-Class: flasher.class

That worked! I can run the generated .jar file with the java -jar flasher.jar command

I also want flasher.jar file to be self contained. I modified manifest.txt and copied the contents of  /Applications/ti/ccsv6/ccs_base/DebugServer/packages/ti/dss/ into the same directory of flasher.jar but I can't get it to run properly. My updated manifest.txt is: 

Main-Class: flasher
Class-Path: . ./java/dss.jar ./*

If I change the Class-Path to the following and create a new .jar file, it runs fine:

Class-Path: . /Applications/ti/ccsv6/ccs_base/DebugServer/packages/ti/dss/java/dss.jar /Applications/ti/ccsv6/ccs_base/DebugServer/packages/ti/dss/

The error I'm getting seems to be when I try to open a debug server session. The line is:

debugSession = debugServer.openSession("Texas Instruments XDS100v2 USB Debug Probe/C28xx_CPU1");

and the error I get is:     SEVERE: Can not connect to DebugServer. Path not found: '/Users/<userName>/<dirOne>/bin'

I'm running the file from: /Users/<userName>/<dirOne>/<dirTwo>/flasher/build/flasher.jar

Should I be including some more files in my directory?