You might be my hair twin.
I have a similar story. Got my hair down to BSL in '09 with Lush Caca Noir to try to mellow out some old highlights. Yes, it did fade quite a bit. I regretted the use of indigo because when I wanted to go lighter I had to cut a lot of length to keep it from going green. Then I was bleaching again until I realized that was truly destroying my hair. Then I did a brown semi permanent to aid in growing out to my natural color. Eventually I started doing henna again, but since it was over my natural hair, it wasn't as bright and didn't have quite the same line of demarcation. Even with henna, I had to keep my hair at shoulder length for about three years to cut off damage. It literally would not grow past there and I was still heat styling, just not as much as before.
As an aside, I think one of the hardest things with our hair color and texture is deciding whether we're brunette, blonde or redhead! Whether we are curly or wavy! We're all of these descriptors...flexible, but kind of fragile!
As someone who has been to bleach and back several times in my life, and used henna over bleach with natural roots coming in, my experience is that it is much more realistic-looking for my hair and skin color to avoid multiple layerings of henna and absolutely avoid indigo and henndigo. I did use a deposit-only color in about a level 5-6 neutral brown on the really bleached lengths. Then using judicious applications of henna (I've alternately used Moroccan and Jamila) I was able to preserve some length without having a weird bright color demarcation. That helped me avoid too much chemical process and get the henna benefits. Once my hair finally stopped literally crumbling off at the ends a couple years ago, I did my Moroccan henna about twice a year, enough for it to fade a bit from the lengths (YMMV -- I am one of those rare birds that does get a bit of fade from henna, but I'm not leaving it on for more than an hour).
All henna is red -- everyone here will tell you that -- and will get more red to purple the more you layer and saturate it. I do notice a difference when I do one-hour applications with Jamila vs. Moroccan -- the Moroccan is browner when not hit with direct light. I'd be careful not to do too many layers of any henna or you'll get too red and then your roots application ritual will take a lot longer and the whole thing may be harder to match up.
I think you CAN even up your lengths after-the-fact with some deposit-only color. I think you might be happier if you do not layer any more henna on what you've got going and just do your roots. You can always slap another full-head layer on in a couple months once you have more grow-out. I've never used Red Raj, so I can't speak to how it is different from Jamila or Moroccan.
I can tell you I will never use indigo on my hair again. I think you and I were chatting on the swap board about Brahmi -- had I known about that herb in 2013, I might have not used any deposit-only color on my bleached bits. Or maybe I would have. Whatever -- I think my old bleach is cut off now and all that's left on me is my bottom four inches that's leftover heat damage. My experience was the Brahmi was not permanent and it did tone down gold/orange and darken, which is exactly what I wanted to do with my old bleach highlights at different points in time. Henndigo was not the right solution for me to correct unwanted highlights.
Your hair is pretty, and it isn't as extreme as you describe!
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