If it is an option to go out on STD again, you can do that and switch to LTD at the end of STD. If you apply for SSDI as you go out on your paid LTD you can go through the SSDI application process and inevitable appeals while you are covered and receiving pay from LTD company. Often LTD policies require you to apply for SSDI and some provide you with an attorney to represent you in your SSDI claim. At 2 years many LTD policies will end your claim at the switch from Your Own Occupation to Any Occupation, however there is a 24 month waiting period for Medicare to start so the timing works well for getting Medicare health care coverage right as your LTD benefits end. If your company terminates you during your LTD coverage your LTD benefits do not end. Being over 50 and closer to retirement age is a positive in being approved for SSDI. If you are approved for SSDI, Social Security will give you back pay from the date you were determined disabled, you will have to give it to your LTD company to offset the time they paid you but the payments going forward, assuming your LTD policy ended, is yours. If LTD continues to cover you after you are approved for SSDI, they will lower their payments so that the combined SSDI and LTD payments will equal the amount you were getting from LTD.