diff --git a/base/client.jl b/base/client.jl
index f7fe7b2d3fad7..7fa89f73ac5ba 100644
--- a/base/client.jl
+++ b/base/client.jl
@@ -273,11 +273,14 @@ function exec_options(opts)
     end
 
     # Maybe redefine bounds checking if requested
-    if JLOptions().check_bounds != 0
-        if JLOptions().check_bounds == 1
-            Core.eval(Main, :(Core.should_check_bounds(boundscheck::Bool) = true))
-        else
-            Core.eval(Main, :(Core.should_check_bounds(boundscheck::Bool) = false))
+    if ccall(:jl_generating_output, Cint, ()) == 0
+        # Inoperative during output generation. Determined by mandatory deps mechanism.
+        if JLOptions().check_bounds != 0
+            if JLOptions().check_bounds == 1
+                require(PkgId(UUID((0xb3a877e5_8181_4b4a, 0x8173_0b9cb13136fe)),"--check-bounds=yes"))
+            else
+                require(PkgId(UUID((0x5ece1bc4_2007_43a8, 0xac47_40059be74678)),"--check-bounds=no"))
+            end
         end
     end
 
diff --git a/base/loading.jl b/base/loading.jl
index facc1d4fbd684..1c95b93dc5662 100644
--- a/base/loading.jl
+++ b/base/loading.jl
@@ -2924,7 +2924,7 @@ function maybe_cachefile_lock(f, pkg::PkgId, srcpath::String; stale_age=300)
             pid, hostname, age = invokelatest(parse_pidfile_hook, pidfile)
             verbosity = isinteractive() ? CoreLogging.Info : CoreLogging.Debug
             if isempty(hostname) || hostname == gethostname()
-                @logmsg verbosity "Waiting for another process (pid: $pid) to finish precompiling $pkg"
+                @logmsg verbosity "Waiting for another process (pid: $pid) to finish precompiling $pkg (pidfile: $pidfile)"
             else
                 @logmsg verbosity "Waiting for another machine (hostname: $hostname, pid: $pid) to finish precompiling $pkg"
             end
diff --git a/pkgimage.mk b/pkgimage.mk
index c9d1cc826dff1..f0e83101db92f 100644
--- a/pkgimage.mk
+++ b/pkgimage.mk
@@ -33,18 +33,24 @@ all-release: $(addprefix cache-release-, $(STDLIBS))
 all-debug:   $(addprefix cache-debug-, $(STDLIBS))
 
 define pkgimg_builder
-$1_SRCS := $$(shell find $$(build_datarootdir)/julia/stdlib/$$(VERSDIR)/$1/src -name \*.jl) \
+PKGIMG_SRCS := $$(shell find "$$(build_datarootdir)/julia/stdlib/$$(VERSDIR)/$1/src" -name \*.jl) \
     $$(wildcard $$(build_prefix)/manifest/$$(VERSDIR)/$1)
-$$(BUILDDIR)/stdlib/$1.release.image: $$($1_SRCS) $$(addsuffix .release.image,$$(addprefix $$(BUILDDIR)/stdlib/,$2)) $(build_private_libdir)/sys.$(SHLIB_EXT)
-#	@$$(call PRINT_JULIA, $$(call spawn,$$(JULIA_EXECUTABLE)) --startup-file=no --check-bounds=yes -e 'Base.compilecache(Base.identify_package("$1"))')
+PKGIMG_SENTINEL_NAME = $(subst =,_EQ_,$1)
+$$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).release.image: $$(PKGIMG_SRCS) $$(addsuffix .release.image,$$(addprefix $$(BUILDDIR)/stdlib/,$2)) $(build_private_libdir)/sys.$(SHLIB_EXT)
 	@$$(call PRINT_JULIA, $$(call spawn,$$(JULIA_EXECUTABLE)) --startup-file=no -e 'Base.compilecache(Base.identify_package("$1"))')
 	touch $$@
-cache-release-$1: $$(BUILDDIR)/stdlib/$1.release.image
-$$(BUILDDIR)/stdlib/$1.debug.image: $$($1_SRCS) $$(addsuffix .debug.image,$$(addprefix $$(BUILDDIR)/stdlib/,$2)) $(build_private_libdir)/sys-debug.$(SHLIB_EXT)
-#	@$$(call PRINT_JULIA, $$(call spawn,$$(JULIA_EXECUTABLE)) --startup-file=no --check-bounds=yes -e 'Base.compilecache(Base.identify_package("$1"))')
+$$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).release.checkbounds.image: $$(PKGIMG_SRCS) $$(addsuffix .release.checkbounds.image,$$(addprefix $$(BUILDDIR)/stdlib/,$2)) $$(BUILDDIR)/stdlib/--check-bounds_EQ_yes.release.image $(build_private_libdir)/sys.$(SHLIB_EXT)
+	@$$(call PRINT_JULIA, $$(call spawn,$$(JULIA_EXECUTABLE)) --startup-file=no --check-bounds=yes -e 'Base.compilecache(Base.identify_package("$1"))')
+	touch $$@
+cache-release-$$(PKGIMG_SENTINEL_NAME): $$(BUILDDIR)/stdlib/$1.release.image $$(BUILDDIR)/stdlib/$1.release.checkbounds.image
+$$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).debug.image: $$(PKGIMG_SRCS) $$(addsuffix .debug.image,$$(addprefix $$(BUILDDIR)/stdlib/,$2)) $(build_private_libdir)/sys-debug.$(SHLIB_EXT)
 	@$$(call PRINT_JULIA, $$(call spawn,$$(JULIA_EXECUTABLE)) --startup-file=no -e 'Base.compilecache(Base.identify_package("$1"))')
-cache-debug-$1: $$(BUILDDIR)/stdlib/$1.debug.image
-.SECONDARY: $$(BUILDDIR)/stdlib/$1.release.image $$(BUILDDIR)/stdlib/$1.debug.image
+	touch $$@
+$$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).debug.checkbounds.image: $$(PKGIMG_SRCS) $$(addsuffix .debug.checkbounds.image,$$(addprefix $$(BUILDDIR)/stdlib/,$2)) $$(BUILDDIR)/stdlib/--check-bounds_EQ_yes.debug.image $(build_private_libdir)/sys-debug.$(SHLIB_EXT)
+	@$$(call PRINT_JULIA, $$(call spawn,$$(JULIA_EXECUTABLE)) --startup-file=no --check-bounds=yes -e 'Base.compilecache(Base.identify_package("$1"))')
+	touch $$@
+cache-debug-$$(PKGIMG_SENTINEL_NAME): $$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).debug.image $$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).debug.checkbounds.image
+.SECONDARY: $$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).release.image $$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).release.checkbounds.image $$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).debug.image $$(BUILDDIR)/stdlib/$$(PKGIMG_SENTINEL_NAME).debug.checkbounds.image
 endef
 
 # Used to just define them in the dependency graph
@@ -52,14 +58,19 @@ endef
 define sysimg_builder
 $$(BUILDDIR)/stdlib/$1.release.image:
 	touch $$@
-cache-release-$1: $$(BUILDDIR)/stdlib/$1.release.image
+$$(BUILDDIR)/stdlib/$1.release.checkbounds.image:
+	touch $$@
+cache-release-$1: $$(BUILDDIR)/stdlib/$1.release.image $$(BUILDDIR)/stdlib/$1.release.checkbounds.image
 $$(BUILDDIR)/stdlib/$1.debug.image:
 	touch $$@
-cache-debug-$1: $$(BUILDDIR)/stdlib/$1.debug.image
-.SECONDARY: $$(BUILDDIR)/stdlib/$1.release.image $$(BUILDDIR)/stdlib/$1.debug.image
+$$(BUILDDIR)/stdlib/$1.debug.checkbounds.image:
+	touch $$@
+cache-debug-$1: $$(BUILDDIR)/stdlib/$1.debug.image $$(BUILDDIR)/stdlib/$1.debug.checkbounds.image
+.SECONDARY: $$(BUILDDIR)/stdlib/$1.release.image $$(BUILDDIR)/stdlib/$1.release.checkbounds.image $$(BUILDDIR)/stdlib/$1.debug.image $$(BUILDDIR)/stdlib/$1.debug.checkbounds.image
 endef
 
 # no dependencies
+$(eval $(call pkgimg_builder,--check-bounds=yes,))
 $(eval $(call pkgimg_builder,MozillaCACerts_jll,))
 $(eval $(call sysimg_builder,ArgTools,))
 $(eval $(call sysimg_builder,Artifacts,))
diff --git a/stdlib/--check-bounds=no/Project.toml b/stdlib/--check-bounds=no/Project.toml
new file mode 100644
index 0000000000000..f5eb68491a096
--- /dev/null
+++ b/stdlib/--check-bounds=no/Project.toml
@@ -0,0 +1,2 @@
+name = "--check-bounds=no"
+uuid = "5ece1bc4-2007-43a8-ac47-40059be74678"
diff --git a/stdlib/--check-bounds=no/src/--check-bounds=no.jl b/stdlib/--check-bounds=no/src/--check-bounds=no.jl
new file mode 100644
index 0000000000000..161ac88fdded4
--- /dev/null
+++ b/stdlib/--check-bounds=no/src/--check-bounds=no.jl
@@ -0,0 +1,8 @@
+__precompile__(:mandatory)
+module var"--check-bounds=no"
+
+@Base.recompile_invalidations begin
+    Core.should_check_bounds(boundscheck::Bool) = false
+end
+
+end
diff --git a/stdlib/--check-bounds=yes/Project.toml b/stdlib/--check-bounds=yes/Project.toml
new file mode 100644
index 0000000000000..81f1391f1478a
--- /dev/null
+++ b/stdlib/--check-bounds=yes/Project.toml
@@ -0,0 +1,2 @@
+name = "--check-bounds=yes"
+uuid = "b3a877e5-8181-4b4a-8173-0b9cb13136fe"
\ No newline at end of file
diff --git a/stdlib/--check-bounds=yes/src/--check-bounds=yes.jl b/stdlib/--check-bounds=yes/src/--check-bounds=yes.jl
new file mode 100644
index 0000000000000..4a8dba504fee5
--- /dev/null
+++ b/stdlib/--check-bounds=yes/src/--check-bounds=yes.jl
@@ -0,0 +1,8 @@
+__precompile__(:mandatory)
+module var"--check-bounds=yes"
+
+@Base.recompile_invalidations begin
+    Core.should_check_bounds(boundscheck::Bool) = true
+end
+
+end
diff --git a/stdlib/Makefile b/stdlib/Makefile
index e42061d593905..5dccd4b628931 100644
--- a/stdlib/Makefile
+++ b/stdlib/Makefile
@@ -43,7 +43,7 @@ $(foreach jll,$(JLLS),$(eval $(call download-artifacts-toml,$(jll))))
 STDLIBS = Artifacts Base64 CRC32c Dates Distributed FileWatching \
           Future InteractiveUtils LazyArtifacts Libdl LibGit2 LinearAlgebra Logging \
           Markdown Mmap Printf Profile Random REPL Serialization \
-          SharedArrays Sockets Test TOML Unicode UUIDs \
+          SharedArrays Sockets Test TOML Unicode UUIDs --check-bounds=yes --check-bounds=no \
           $(JLL_NAMES)
 
 STDLIBS_EXT = Pkg Statistics LibCURL DelimitedFiles Downloads ArgTools Tar NetworkOptions SuiteSparse SparseArrays SHA