Expatriate success stories did not always run smoothly; this chapter shows how Edgar Wilson’s class transformation was beset by anxiety around real and imagined tensions with elite management figures in London and Persia. It also charts a delayed pre-war honeymoon trip to England through Russia. But work stresses on Wilson’s career extended to his marriage, forcing long periods of reluctant separation and hazardous risks to the family in southern Persia during World War One. It elucidates a key stage in the progression of the Wilsons’ social mobility under expatriate conditions, charting events impacting Middle East shipping during the war and after, told through Edgar and Winfred’s correspondence and diaries, including sexually explicit love letters, and a perilous family trek on mules across Persian mountains. For Winifred, the experience of childbirth in Tehran early in the marriage and in England, her experience of stepmothering without Edgar, marked a steep learning curve, influencing the marriage for years ahead. Spousal correspondence is a highlight of this chapter, with intimate insights into marriage and its cosmopolitan growth under the influence of expatriation and marital sexuality.