The synthesis of polyamines is often a laborious task that usually requires the use of complex protection schemes in combination with harsh alkylation steps. Here, we report the development of a convenient strategy for the generation of various linear as well as branched lipophilic polyamine structures on solid phase. The sequential use of Aloc-, o-nosyl-, and Dde groups for differentiation between the primary and secondary amines and Fukuyama alkylation and reductive amination for elongation and modification of the backbone enabled the synthesis of both, linear as well as branched polyamines. The mild deprotection conditions facilitated the synthesis of acid- and base-labile conjugates. This strategy was applied for the synthesis of a range of fluorescently labelled polyamine conjugates with varying degrees of lipophilic substitution.