Good day, I am seeking advice/information from those that have been in similar positions in the military, are very knowledgeable about the Montgomery/Post 911 GI Bill funding, and/or have had to make similar choices within the system. I am at right around 15 years of active duty and I still have maintained my Montgomery GI Bill and have not transferred over to Post 911, yet. The main reason is because I haven't been forced to make the choice yet and I am aware of the potential benefit of using all of the entitlement under Montgomery and getting an additional year of Post 911 afterwards, maybe for additional educational funds overall, depending on how it is used. Since I am still active duty I have been able to use tuition assistance, with minimal out of pocket expenses, for both my BA and my MS. I am about 5 years out from being eligible for retirement, though I can likely go another 15 years or so before forced retirement, but I am planning for now to be ready to depart at around 20. As far as education, I have mostly done it up to this point for personal satisfaction and to use within my daily work with an eventual hope to use the degrees post retirement. If I go into a PhD program now I have the option of using Montgomery GI Bill, switching to Post 911 (with Yellow Ribbon) and using it, or trying to pay out of pocket. I know using the GI Bill program now leaves money on the table, the trade off long-term may be worth it and is what I am trying to figure out. Has anyone been in a similar position? My ultimate goal is to get the most value from the GI Bill program. Long-term options I have are to wait until after retirement to take full advantage of the housing and book stipend or to allocate a percentage of the Post-911 GI Bill to each of my children (aged 11 and 7) though I plan on using options to keep their education inexpensive and they are likely to have other scholarship opportunities as well. Ideally, I would be close to completion near retirement and be building my second career opportunities between now and then.... not retiring and then starting a lengthy program. I will likely be in a position next year to have the Service pay 100% for a another graduate degree to attend full time as my only responsibility for the next 12 - 36 months. While this is definitely appealing, it will be either for a JD or a MS/MA in Human Resources Management or I/O Psychology. Both programs interest me and have been long-term goals, but there are some career tradeoffs by accepting the opportunity. I know there is a lot to sort through there, thank you in advance for your time. Thoughts?