I Need Perspective on "Learning Tools"

I need some feedback on whether I am way off on this or not.  I teach middle school math and for the first time in 8 years, I am not also teaching science.  I have also volunteered to work with the eighth grade students who struggle the most in math to help build their confidence, teach them how to think mathematically and get them ready for a fast paced 9th grade Algebra 1 class.  This class was supposed to have the 23 lowest students, however, the other classes that period we too large so they added another 13 pre-algebra 8th graders so now it is a class of 36 math phobic middle school students. 

I am working my tail off to help these kiddos and make learning math a positive experience for them.  I am up against some interesting attitudes.  These kids have been failing math for at least the past three years or more.  They see math as a bunch of meaningless rules that are all mixed up in their brain.  They see themselves as stupid and have no confidence in their ability to think mathematically or "do" math.

When I spend time helping them by asking questions and guiding their thinking, they show me they can think mathematically, however I don't see the lightbulb go off or hear the "OHHHH".  They prove to me everyday that they have math understanding, but they are almost shocked and surprised when they realize they have it.  It is almost like the movie 50 first dates, everyday they walk in not remembering the success they had the day before - success amnesia.

So, my questions...
I am wanting to build their confidence by letting them use tools - calculators, computers, smart phones, iPods, etc...  It is my belief that if their lack of confidence and skills is getting in the way of their showing understanding on the grade level content standards then why not let them use a calculator?  If they use the tool to prove that they do understand, then they will eventually no longer need to rely on it.  I would combine the use with explanations of understanding and by having the students write exactly what is being put into the calculator.  I need the students to see for themselves that they can do it.  They have felt for so long that they can't be successful in math so they do not even try.  I'm getting pressure from my math department on a variety of issues - standards based grading, using tools, making real life math connections, using computer collaboration tools, etc...  Am I way off on this one?  Any other suggestions?

I appreciate ANY feedback my PLN can provide!
Thanks!