Second language (L2) request production has long been a central area of inquiry in interlanguage pragmatics, including how L2 learners mitigate their requests and whether such strategies correspond to or differ from those of first language (L1) speakers. Methodologically, such research often involves elicited speech and tends to isolate the speech act from the surrounding discourse using instruments such as discourse completion tasks. While some naturalistic speech contexts (e.g., academic advising sessions) have been investigated, few studies to date have analyzed requesting in synchronous computer-mediated communication (SCMC). The current study responds by presenting a multifactorial analysis of L1 and L2 request production that occurred during eight one-hour web conferences between L2 learners of German for professional purposes and L1 German professionals. Three taxonomies traditionally used in face-to-face pragmatics research were adapted for analysis of the SCMC, enabling the use of a generalized linear mixed model. Findings indicate that while both groups of speakers used predominantly direct requesting behavior, L1 speakers used significantly more internal modification devices than did L2 learners.