diff --git a/Makefile b/Makefile
index 6360636e..8ddf1e32 100644
--- a/Makefile
+++ b/Makefile
@@ -122,8 +122,10 @@ JANET_BOOT_SOURCES=src/boot/array_test.c \
 				   src/boot/number_test.c \
 				   src/boot/system_test.c \
 				   src/boot/table_test.c
+JANET_BOOT_HEADERS=src/boot/tests.h
 
 JANET_MAINCLIENT_SOURCES=src/mainclient/line.c src/mainclient/main.c
+JANET_MAINCLIENT_HEADERS=src/mainclient/line.h
 
 JANET_WEBCLIENT_SOURCES=src/webclient/main.c
 
@@ -134,6 +136,8 @@ JANET_WEBCLIENT_SOURCES=src/webclient/main.c
 JANET_BOOT_OBJECTS=$(patsubst src/%.c,build/%.boot.o,$(JANET_CORE_SOURCES) $(JANET_BOOT_SOURCES)) \
 	build/boot.gen.o
 
+$(JANET_BOOT_OBJECTS): $(JANET_BOOT_HEADERS)
+
 build/%.boot.o: src/%.c $(JANET_HEADERS) $(JANET_LOCAL_HEADERS)
 	$(CC) $(CFLAGS) -DJANET_BOOTSTRAP -o $@ -c $<
 
@@ -151,6 +155,8 @@ build/core_image.c: build/janet_boot
 JANET_CORE_OBJECTS=$(patsubst src/%.c,build/%.o,$(JANET_CORE_SOURCES)) build/core_image.o
 JANET_MAINCLIENT_OBJECTS=$(patsubst src/%.c,build/%.o,$(JANET_MAINCLIENT_SOURCES))
 
+$(JANET_MAINCLIENT_OBJECTS): $(JANET_MAINCLIENT_HEADERS)
+
 # Compile the core image generated by the bootstrap build
 build/core_image.o: build/core_image.c $(JANET_HEADERS) $(JANET_LOCAL_HEADERS)
 	$(CC) $(CFLAGS) -o $@ -c $<