Traceability is a key enabler of various activities in automotive software and systems engineering and required by several standards. However, most existing traceability management approaches do not consider that traceability is situated in constantly changing development contexts involving multiple stakeholders. Together with an automotive supplier, we analyzed how technology, business, and organizational factors raise the need for flexible traceability. We present how traceability can be evolved in the development lifecycle, from early elicitation of traceability needs to the implementation of mature traceability strategies. Moreover, we shed light on how traceability can be managed flexibly within an agile team and more formally when crossing team borders and organizational borders. Based on these insights, we present requirements for flexible tool solutions, supporting varying levels of data quality, change propagation, versioning, and organizational traceability.