> rpki-client seems to be the one-off under regress/ in this regard.

Maybe. I wish I had a better idea than this

Index: Makefile
===================================================================
RCS file: /cvs/src/regress/usr.sbin/rpki-client/Makefile,v
retrieving revision 1.10
diff -u -p -r1.10 Makefile
--- Makefile    9 Nov 2020 15:49:48 -0000       1.10
+++ Makefile    7 Nov 2021 23:59:10 -0000
@@ -1,7 +1,8 @@
 # $OpenBSD: Makefile,v 1.10 2020/11/09 15:49:48 tb Exp $
 
 SUBDIR += libressl
-.if exists(/usr/local/bin/eopenssl11)
+.if exists(/usr/local/bin/eopenssl11) || \
+       make(obj) || make(clean) || make(cleandir)
 SUBDIR += openssl11
 .else
 .END:

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