diff --git a/3.0/bullseye/Dockerfile b/3.0/bullseye/Dockerfile
index 3b917a955..a348d95d8 100644
--- a/3.0/bullseye/Dockerfile
+++ b/3.0/bullseye/Dockerfile
@@ -64,9 +64,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.0/buster/Dockerfile b/3.0/buster/Dockerfile
index 03abed05f..0f67902bd 100644
--- a/3.0/buster/Dockerfile
+++ b/3.0/buster/Dockerfile
@@ -64,9 +64,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.0/slim-bullseye/Dockerfile b/3.0/slim-bullseye/Dockerfile
index 26b331f68..66ab15e3c 100644
--- a/3.0/slim-bullseye/Dockerfile
+++ b/3.0/slim-bullseye/Dockerfile
@@ -91,9 +91,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.0/slim-buster/Dockerfile b/3.0/slim-buster/Dockerfile
index 9f755b058..956097c48 100644
--- a/3.0/slim-buster/Dockerfile
+++ b/3.0/slim-buster/Dockerfile
@@ -91,9 +91,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.1/buster/Dockerfile b/3.1/bookworm/Dockerfile
similarity index 94%
rename from 3.1/buster/Dockerfile
rename to 3.1/bookworm/Dockerfile
index f50561f2a..97991aa81 100644
--- a/3.1/buster/Dockerfile
+++ b/3.1/bookworm/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM buildpack-deps:buster
+FROM buildpack-deps:bookworm
 
 # skip installing gem documentation
 RUN set -eux; \
@@ -64,9 +64,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.1/bullseye/Dockerfile b/3.1/bullseye/Dockerfile
index 5851055de..80f0ec1ad 100644
--- a/3.1/bullseye/Dockerfile
+++ b/3.1/bullseye/Dockerfile
@@ -64,9 +64,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.1/slim-buster/Dockerfile b/3.1/slim-bookworm/Dockerfile
similarity index 95%
rename from 3.1/slim-buster/Dockerfile
rename to 3.1/slim-bookworm/Dockerfile
index 887f3916a..fef9c14ad 100644
--- a/3.1/slim-buster/Dockerfile
+++ b/3.1/slim-bookworm/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM debian:buster-slim
+FROM debian:bookworm-slim
 
 RUN set -eux; \
 	apt-get update; \
@@ -91,9 +91,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.1/slim-bullseye/Dockerfile b/3.1/slim-bullseye/Dockerfile
index 9551c6b9b..346266152 100644
--- a/3.1/slim-bullseye/Dockerfile
+++ b/3.1/slim-bullseye/Dockerfile
@@ -91,9 +91,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.2/buster/Dockerfile b/3.2/bookworm/Dockerfile
similarity index 96%
rename from 3.2/buster/Dockerfile
rename to 3.2/bookworm/Dockerfile
index 48d07be31..b56f1ce1f 100644
--- a/3.2/buster/Dockerfile
+++ b/3.2/bookworm/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM buildpack-deps:buster
+FROM buildpack-deps:bookworm
 
 # skip installing gem documentation
 RUN set -eux; \
@@ -88,9 +88,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.2/bullseye/Dockerfile b/3.2/bullseye/Dockerfile
index 47d83c1c2..d4d54ffdc 100644
--- a/3.2/bullseye/Dockerfile
+++ b/3.2/bullseye/Dockerfile
@@ -88,9 +88,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.2/slim-buster/Dockerfile b/3.2/slim-bookworm/Dockerfile
similarity index 96%
rename from 3.2/slim-buster/Dockerfile
rename to 3.2/slim-bookworm/Dockerfile
index 4eae3f543..9adf74dee 100644
--- a/3.2/slim-buster/Dockerfile
+++ b/3.2/slim-bookworm/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM debian:buster-slim
+FROM debian:bookworm-slim
 
 RUN set -eux; \
 	apt-get update; \
@@ -115,9 +115,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.2/slim-bullseye/Dockerfile b/3.2/slim-bullseye/Dockerfile
index 6ca0fa293..775022ad6 100644
--- a/3.2/slim-bullseye/Dockerfile
+++ b/3.2/slim-bullseye/Dockerfile
@@ -115,9 +115,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.3-rc/buster/Dockerfile b/3.3-rc/bookworm/Dockerfile
similarity index 96%
rename from 3.3-rc/buster/Dockerfile
rename to 3.3-rc/bookworm/Dockerfile
index 905a428f5..9159abc49 100644
--- a/3.3-rc/buster/Dockerfile
+++ b/3.3-rc/bookworm/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM buildpack-deps:buster
+FROM buildpack-deps:bookworm
 
 # skip installing gem documentation
 RUN set -eux; \
@@ -88,9 +88,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.3-rc/bullseye/Dockerfile b/3.3-rc/bullseye/Dockerfile
index ef2b7ce22..eedcf34f6 100644
--- a/3.3-rc/bullseye/Dockerfile
+++ b/3.3-rc/bullseye/Dockerfile
@@ -88,9 +88,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.3-rc/slim-buster/Dockerfile b/3.3-rc/slim-bookworm/Dockerfile
similarity index 96%
rename from 3.3-rc/slim-buster/Dockerfile
rename to 3.3-rc/slim-bookworm/Dockerfile
index 236bf39d9..c116a3678 100644
--- a/3.3-rc/slim-buster/Dockerfile
+++ b/3.3-rc/slim-bookworm/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM debian:buster-slim
+FROM debian:bookworm-slim
 
 RUN set -eux; \
 	apt-get update; \
@@ -114,9 +114,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/3.3-rc/slim-bullseye/Dockerfile b/3.3-rc/slim-bullseye/Dockerfile
index 7a38e1fe1..c2f6993de 100644
--- a/3.3-rc/slim-bullseye/Dockerfile
+++ b/3.3-rc/slim-bullseye/Dockerfile
@@ -114,9 +114,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/Dockerfile.template b/Dockerfile.template
index 33ecb3b5f..c81cc16bd 100644
--- a/Dockerfile.template
+++ b/Dockerfile.template
@@ -262,9 +262,8 @@ RUN set -eux; \
 	apt-mark auto '.*' > /dev/null; \
 	apt-mark manual $savedAptMark > /dev/null; \
 	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
-		| awk '/=>/ { print $(NF-1) }' \
+		| awk '/=>/ { so = $(NF-1); if (index(so, "/usr/local/") == 1) { next }; gsub("^/(usr/)?", "", so); print so }' \
 		| sort -u \
-		| grep -vE '^/usr/local/lib/' \
 		| xargs -r dpkg-query --search \
 		| cut -d: -f1 \
 		| sort -u \
diff --git a/versions.json b/versions.json
index 04f7764c5..40cd75918 100644
--- a/versions.json
+++ b/versions.json
@@ -13,10 +13,10 @@
   "3.1": {
     "sha256": "1b6d6010e76036c937b9671f4752f065aeca800a6c664f71f6c9a699453af94f",
     "variants": [
+      "bookworm",
+      "slim-bookworm",
       "bullseye",
       "slim-bullseye",
-      "buster",
-      "slim-buster",
       "alpine3.18",
       "alpine3.17"
     ],
@@ -57,10 +57,10 @@
     },
     "sha256": "4b352d0f7ec384e332e3e44cdbfdcd5ff2d594af3c8296b5636c710975149e23",
     "variants": [
+      "bookworm",
+      "slim-bookworm",
       "bullseye",
       "slim-bullseye",
-      "buster",
-      "slim-buster",
       "alpine3.18",
       "alpine3.17"
     ],
@@ -101,10 +101,10 @@
     },
     "sha256": "ae300b49e06c13087dd163b97eddd38db895dc8e0c9904284119795d75303fbb",
     "variants": [
+      "bookworm",
+      "slim-bookworm",
       "bullseye",
       "slim-bullseye",
-      "buster",
-      "slim-buster",
       "alpine3.18",
       "alpine3.17"
     ],
diff --git a/versions.sh b/versions.sh
index 090102643..d887f0c73 100755
--- a/versions.sh
+++ b/versions.sh
@@ -70,9 +70,16 @@ for version in "${versions[@]}"; do
 			sha256: env.shaVal,
 			variants: [
 				(
-					"bullseye",
-					"buster",
-					empty # trailing comma hack
+					# https://bugs.ruby-lang.org/issues/18658
+					# https://github.com/docker-library/ruby/pull/392#issuecomment-1329896174
+					if  "3.0" == env.version then
+						"bullseye",
+						"buster"
+					else
+						"bookworm",
+						"bullseye",
+						empty # trailing comma hack
+					end
 				| ., "slim-" + .), # https://github.com/docker-library/ruby/pull/142#issuecomment-320012893
 				(
 					# Alpine 3.17+ defaults to OpenSSL 3 which is not supported by Ruby 3.0