diff --git a/sys-libs/readline/readline-8.2_p13-r1.ebuild b/sys-libs/readline/readline-8.2_p13-r1.ebuild
index 29f55a7d24fbb..760a2f6b73007 100644
--- a/sys-libs/readline/readline-8.2_p13-r1.ebuild
+++ b/sys-libs/readline/readline-8.2_p13-r1.ebuild
@@ -126,7 +126,7 @@ src_prepare() {
 
 	is_release || eautoreconf
 
-	if use prefix && [[ -n ${STAGE} ]] ; then
+	if use prefix && ! type -P $(tc-getPKG_CONFIG) > /dev/null ; then
 		# If we're bootstrapping, make a guess. We don't have pkg-config
 		# around yet. bug #818103.
 		# Incorrectly populating this leads to underlinked libreadline.
diff --git a/sys-libs/readline/readline-8.3_p3.ebuild b/sys-libs/readline/readline-8.3_p3.ebuild
index 3fddcda052544..c8f52140a0004 100644
--- a/sys-libs/readline/readline-8.3_p3.ebuild
+++ b/sys-libs/readline/readline-8.3_p3.ebuild
@@ -126,7 +126,7 @@ src_prepare() {
 
 	#(( PLEVEL < 0 )) && eautoreconf
 
-	if use prefix && [[ -n ${STAGE} ]] ; then
+	if use prefix && ! type -P $(tc-getPKG_CONFIG) > /dev/null ; then
 		# If we're bootstrapping, make a guess. We don't have pkg-config
 		# around yet. bug #818103.
 		# Incorrectly populating this leads to underlinked libreadline.
diff --git a/sys-libs/readline/readline-8.4_alpha_pre20251007.ebuild b/sys-libs/readline/readline-8.4_alpha_pre20251007.ebuild
index b6cfe4de3649e..2450df74c0741 100644
--- a/sys-libs/readline/readline-8.4_alpha_pre20251007.ebuild
+++ b/sys-libs/readline/readline-8.4_alpha_pre20251007.ebuild
@@ -126,7 +126,7 @@ src_prepare() {
 
 	#(( PLEVEL < 0 )) && eautoreconf
 
-	if use prefix && [[ -n ${STAGE} ]] ; then
+	if use prefix && ! type -P $(tc-getPKG_CONFIG) > /dev/null ; then
 		# If we're bootstrapping, make a guess. We don't have pkg-config
 		# around yet. bug #818103.
 		# Incorrectly populating this leads to underlinked libreadline.
diff --git a/sys-libs/readline/readline-9999.ebuild b/sys-libs/readline/readline-9999.ebuild
index 236229ef6d735..24a840f7f08a9 100644
--- a/sys-libs/readline/readline-9999.ebuild
+++ b/sys-libs/readline/readline-9999.ebuild
@@ -126,7 +126,7 @@ src_prepare() {
 
 	#(( PLEVEL < 0 )) && eautoreconf
 
-	if use prefix && [[ -n ${STAGE} ]] ; then
+	if use prefix && ! type -P $(tc-getPKG_CONFIG) > /dev/null ; then
 		# If we're bootstrapping, make a guess. We don't have pkg-config
 		# around yet. bug #818103.
 		# Incorrectly populating this leads to underlinked libreadline.