A cable transition device includes a support sleeve and a sealing member. The support sleeve is configured to be inserted between a structural overwrap and a compliant outer jacket of a coaxial cable, wherein the compliant outer jacket surrounds signal-carrying conductors and extends beyond a terminal end of a stepped transition. The sealing member is configured to be disposed over the stepped transition of the coaxial cable so as to seal the stepped transition portion of the coaxial cable during operation of the cable transition device.