diff --git a/share/mk/bsd.compiler.mk b/share/mk/bsd.compiler.mk
--- a/share/mk/bsd.compiler.mk
+++ b/share/mk/bsd.compiler.mk
@@ -235,7 +235,7 @@
 ${X_}COMPILER_FEATURES+=	c++17
 .endif
 .if ${${X_}COMPILER_TYPE} == "clang"
-${X_}COMPILER_FEATURES+=	retpoline init-all
+${X_}COMPILER_FEATURES+=	compressed-debug retpoline init-all
 .endif
 .if ${${X_}COMPILER_TYPE} == "clang" && ${${X_}COMPILER_VERSION} >= 100000 || \
 	(${${X_}COMPILER_TYPE} == "gcc" && ${${X_}COMPILER_VERSION} >= 80100)
diff --git a/share/mk/bsd.lib.mk b/share/mk/bsd.lib.mk
--- a/share/mk/bsd.lib.mk
+++ b/share/mk/bsd.lib.mk
@@ -113,8 +113,13 @@
 
 .if ${MK_DEBUG_FILES} != "no" && empty(DEBUG_FLAGS:M-g) && \
     empty(DEBUG_FLAGS:M-gdwarf*)
+.if !${COMPILER_FEATURES:Mcompressed-debug}
+CFLAGS+= ${DEBUG_FILES_CFLAGS:N-gz*}
+CXXFLAGS+= ${DEBUG_FILES_CFLAGS:N-gz*}
+.else
 CFLAGS+= ${DEBUG_FILES_CFLAGS}
 CXXFLAGS+= ${DEBUG_FILES_CFLAGS}
+.endif
 CTFFLAGS+= -g
 .endif
 
diff --git a/share/mk/bsd.prog.mk b/share/mk/bsd.prog.mk
--- a/share/mk/bsd.prog.mk
+++ b/share/mk/bsd.prog.mk
@@ -93,7 +93,11 @@
 .else
 .if ${MK_DEBUG_FILES} != "no" && empty(DEBUG_FLAGS:M-g) && \
     empty(DEBUG_FLAGS:M-gdwarf-*)
+.if !${COMPILER_FEATURES:Mcompressed-debug}
+CFLAGS+= ${DEBUG_FILES_CFLAGS:N-gz*}
+.else
 CFLAGS+= ${DEBUG_FILES_CFLAGS}
+.endif
 CTFFLAGS+= -g
 .endif
 .endif
diff --git a/share/mk/bsd.sys.mk b/share/mk/bsd.sys.mk
--- a/share/mk/bsd.sys.mk
+++ b/share/mk/bsd.sys.mk
@@ -247,7 +247,7 @@
 
 # Additional flags passed in CFLAGS and CXXFLAGS when MK_DEBUG_FILES is
 # enabled.
-DEBUG_FILES_CFLAGS?= -g
+DEBUG_FILES_CFLAGS?= -g -gz=zlib
 
 # Allow user-specified additional warning flags, plus compiler and file
 # specific flag overrides, unless we've overridden this...