diff --git a/programs/zstdless b/programs/zstdless
index 893799e7d95..17726a4f6e1 100755
--- a/programs/zstdless
+++ b/programs/zstdless
@@ -1,2 +1,8 @@
 #!/bin/sh
-zstdcat "$@" | less
+
+zstd=${ZSTD:-zstd}
+
+# TODO: Address quirks and bugs tied to old versions of less, provide a mechanism to pass flags directly to zstd
+
+export LESSOPEN="|-${zstd} -cdfq %s"
+exec less "$@"
diff --git a/tests/Makefile b/tests/Makefile
index 132fa7a0818..e3a69b65a61 100644
--- a/tests/Makefile
+++ b/tests/Makefile
@@ -288,7 +288,7 @@ list:
 
 .PHONY: shortest
 shortest: ZSTDRTTEST=  # remove long tests
-shortest: test-zstd
+shortest: test-zstd test-zstdtools
 
 .PHONY: check
 check: shortest
@@ -297,7 +297,7 @@ check: shortest
 fuzztest: test-fuzzer test-zstream test-decodecorpus
 
 .PHONY: test
-test: test-zstd test-fullbench test-fuzzer test-zstream test-invalidDictionaries test-legacy test-decodecorpus
+test: test-zstd test-zstdtools test-fullbench test-fuzzer test-zstream test-invalidDictionaries test-legacy test-decodecorpus
 ifeq ($(QEMU_SYS),)
 test: test-pool
 endif
@@ -308,7 +308,7 @@ test32: test-zstd32 test-fullbench32 test-fuzzer32 test-zstream32
 .PHONY: test-all
 test-all: test test32 valgrindTest test-decodecorpus-cli
 
-.PHONY: test-zstd test-zstd32 test-zstd-nolegacy test-zstdgrep
+.PHONY: test-zstd test-zstd32 test-zstdtools test-zstd-nolegacy test-zstdgrep
 test-zstd: ZSTD = $(PRGDIR)/zstd
 test-zstd: zstd
 
@@ -322,6 +322,12 @@ test-zstd test-zstd32 test-zstd-nolegacy: datagen
 	file $(ZSTD)
 	EXE_PREFIX="$(QEMU_SYS)" ZSTD_BIN="$(ZSTD)" DATAGEN_BIN=./datagen ./playTests.sh $(ZSTDRTTEST)
 
+test-zstdtools: ZSTD = $(PRGDIR)/zstd
+
+test-zstdtools: zstd
+	file $(ZSTD)
+	ZSTD_BIN="$(ZSTD)" ./playToolTests.sh
+
 test-fullbench: fullbench datagen
 	$(QEMU_SYS) ./fullbench -i1
 	$(QEMU_SYS) ./fullbench -i1 -P0
diff --git a/tests/a.txt b/tests/a.txt
new file mode 100644
index 00000000000..3ded3d49b52
--- /dev/null
+++ b/tests/a.txt
@@ -0,0 +1,4 @@
+asdf
+
+
+jkl
diff --git a/tests/playTests.sh b/tests/playTests.sh
index b7a3d88a817..0540a94fae2 100755
--- a/tests/playTests.sh
+++ b/tests/playTests.sh
@@ -88,7 +88,6 @@ SCRIPT_DIR=$(cd "$(dirname "$0")" && pwd)
 PRGDIR="$SCRIPT_DIR/../programs"
 TESTDIR="$SCRIPT_DIR/../tests"
 UNAME=$(uname)
-ZSTDGREP="$PRGDIR/zstdgrep"
 
 detectedTerminal=false
 if [ -t 0 ] && [ -t 1 ]
@@ -311,17 +310,6 @@ if [ "$isWindows" = false ]; then
   fi
 fi
 
-println "\n===> zstdgrep tests"
-ln -sf "$ZSTD_BIN" zstdcat
-rm -f tmp_grep
-echo "1234" > tmp_grep
-zstd -f tmp_grep
-lines=$(ZCAT=./zstdcat "$ZSTDGREP" 2>&1 "1234" tmp_grep tmp_grep.zst | wc -l)
-test 2 -eq $lines
-ZCAT=./zstdcat "$ZSTDGREP" 2>&1 "1234" tmp_grep_bad.zst && die "Should have failed"
-ZCAT=./zstdcat "$ZSTDGREP" 2>&1 "1234" tmp_grep_bad.zst | grep "No such file or directory" || true
-rm -f tmp_grep*
-
 println "\n===>  --exclude-compressed flag"
 rm -rf precompressedFilterTestDir
 mkdir -p precompressedFilterTestDir
diff --git a/tests/playToolTests.sh b/tests/playToolTests.sh
new file mode 100755
index 00000000000..12c08ffe9d6
--- /dev/null
+++ b/tests/playToolTests.sh
@@ -0,0 +1,87 @@
+#!/bin/sh
+
+set -e
+
+die() {
+    println "$@" 1>&2
+    exit 1
+}
+
+zstd() {
+    if [ -z "$EXEC_PREFIX" ]; then
+        "$ZSTD_BIN" "$@"
+    else
+        "$EXEC_PREFIX" "$ZSTD_BIN" "$@"
+    fi
+}
+
+println() {
+    printf '%b\n' "${*}"
+}
+
+SCRIPT_DIR=$(cd "$(dirname "$0")" && pwd)
+PRGDIR="$SCRIPT_DIR/../programs"
+UNAME=$(uname)
+ZSTDGREP="$PRGDIR/zstdgrep"
+ZSTDLESS="$PRGDIR/zstdless"
+
+INTOVOID="/dev/null"
+case "$UNAME" in
+  GNU) DEVDEVICE="/dev/random" ;;
+  *) DEVDEVICE="/dev/zero" ;;
+esac
+case "$OS" in
+  Windows*)
+    INTOVOID="NUL"
+    DEVDEVICE="NUL"
+    ;;
+esac
+
+DIFF="diff"
+case "$UNAME" in
+  SunOS) DIFF="gdiff" ;;
+esac
+
+# check if ZSTD_BIN is defined. if not, use the default value
+if [ -z "${ZSTD_BIN}" ]; then
+  println "\nZSTD_BIN is not set. Using the default value..."
+  ZSTD_BIN="$PRGDIR/zstd"
+fi
+
+# assertions
+[ -n "$ZSTD_BIN" ] || die "zstd not found at $ZSTD_BIN! \n Please define ZSTD_BIN pointing to the zstd binary. You might also consider rebuilding zstd following the instructions in README.md"
+println "\nStarting playToolTests.sh EXE_PREFIX='$EXE_PREFIX' ZSTD_BIN='$ZSTD_BIN' DATAGEN_BIN='$DATAGEN_BIN'"
+
+
+
+# tool tests
+
+println "\n===> zstdgrep tests"
+ln -sf "$ZSTD_BIN" zstdcat
+rm -f tmp_grep
+echo "1234" > tmp_grep
+zstd -f tmp_grep
+lines=$(ZCAT=./zstdcat "$ZSTDGREP" 2>&1 "1234" tmp_grep tmp_grep.zst | wc -l)
+test 2 -eq $lines
+ZCAT=./zstdcat "$ZSTDGREP" 2>&1 "1234" tmp_grep_bad.zst && die "Should have failed"
+ZCAT=./zstdcat "$ZSTDGREP" 2>&1 "1234" tmp_grep_bad.zst | grep "No such file or directory" || true
+rm -f tmp_grep*
+
+println "\n===> zstdless tests"
+if [ -n "$(which less)" ]; then
+  ln -sf "$ZSTD_BIN" zstd
+  rm -f tmp_less*
+  echo "1234" > tmp_less
+  echo "foo" >> tmp_less
+  echo "bar" >> tmp_less
+  less -N -f tmp_less > tmp_less_counted
+  zstd -f tmp_less
+  lines=$(ZSTD=./zstd "$ZSTDLESS" 2>&1 tmp_less.zst | wc -l)
+  test 3 -eq $lines
+  ZSTD=./zstd "$ZSTDLESS" -f tmp_less.zst > tmp_less_regenerated
+  $DIFF tmp_less tmp_less_regenerated
+  ZSTD=./zstd "$ZSTDLESS" -N -f tmp_less.zst > tmp_less_regenerated_counted
+  $DIFF tmp_less_counted tmp_less_regenerated_counted
+  ZSTD=./zstd "$ZSTDLESS" 2>&1 tmp_less_bad.zst | grep "No such file or directory" || die
+  rm -f tmp_less*
+fi