This paper outlines issues and emerging themes from two recent case studies conducted in similar yet contrasting highly disadvantaged communities in South Yorkshire, U.K. Both groups of schools were viewed as broadly successful in tackling the range of issues impacting locally, and in providing positive outcomes for their young people. They were both located in the top five percent of most deprived areas nationally, with one community being "multi-cultural" and the other predominantly "white working class".The methodological approach was essentially interpretive/phenomenological, aiming to make a contribution to theory through the use of grounded methods and the study of phenomena in their natural settings. The studies employed three main qualitative techniques: open- ended interviews with key individuals at regular intervals, semi-structured interviews and a small number of observation studies. The research outcomes encompass both dilemmas and extremely problematic practical issues concerning leadership and practice in these chools/communities, particularly:- The nature of leadership strength required in these situations;- The fragility of leadership and school progress, yet the extreme need for hope;- The need for both leadership idealism and pragmatism;- The dilemmas and difficulties associated with adopting child-centred approaches in these schools;- The difficulty yet leadership necessity of working with parents and the surrounding community; - The nature of the leadership task in raising horizons and expectations to enable young people to reach their educational potential;- The political leadership task involved in work with other agencies locally; and -The leadership imperative of raising and then maintaining a school's reputation, often from a low base. Differences between the approaches to and experience of the education process in these two similarly deprived communities were noteworthy, particularly:- The different way they approached the behaviour issue, with one family of schools specifically focusing on it, and the other deliberately not doing so;- The differing perceived degrees of fragility of the two areas' schools, in spite of similar socio-economic indicators;- The ways in which the history of school fragility and progress in both communities potentially had a different impact on current performance;- The perceived difference in approach between both communities' schools: one being arguably more "pragmatic" in approach than the other;- The differential impact of parental choice on the two communities' secondary schools; and,- The perceived differences in outcomes concerning community engagement between the two sets of schools. The paper, finally, seeks to identify best practice examples from the study which can potentially be applied to other similar situations, including in other European countries:- Examples of perceived outstanding school leadership, particularly bearing in mind the challenging context-The fostering of very positive parental/community engagement- Schools and their leaders being important agents of community regeneration-Practical ways in which the perceived critical mass of pupil disaffection in schools can be overcome, and-Ways in which schools in highly disadvantaged communities can remain genuinely "community schools" with comprehensive intakes, in an increasingly competitive and marketised education system.