CA PPM 14.2, on-prem.
Start by noting the 2015 milestones showing in Schedule Gantt as 2014:
Rolling Date is set to blank, where hint text indicates leaving field blank will enable 'auto-fit.'
Work Around: Change Rolling Date to non-blank (e.g. 'start of current year,' 'start of current quarter'...) the images display in their correct position on the Schedule Gantt:
Dale