diff --git a/tests/scenarios/cmd/cut/help/help_flag.yaml b/tests/scenarios/cmd/cut/help/help_flag.yaml
new file mode 100644
index 00000000..e304cd40
--- /dev/null
+++ b/tests/scenarios/cmd/cut/help/help_flag.yaml
@@ -0,0 +1,10 @@
+description: cut --help prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    cut --help
+expect:
+  stdout_contains: ["Usage: cut"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/echo/help/help_flag.yaml b/tests/scenarios/cmd/echo/help/help_flag.yaml
new file mode 100644
index 00000000..0b776925
--- /dev/null
+++ b/tests/scenarios/cmd/echo/help/help_flag.yaml
@@ -0,0 +1,9 @@
+description: echo --help is not recognised as a flag and is printed as literal text.
+input:
+  script: |+
+    echo --help
+expect:
+  stdout: |+
+    --help
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/head/help/help_flag.yaml b/tests/scenarios/cmd/head/help/help_flag.yaml
new file mode 100644
index 00000000..d2ccd94e
--- /dev/null
+++ b/tests/scenarios/cmd/head/help/help_flag.yaml
@@ -0,0 +1,10 @@
+description: head --help prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    head --help
+expect:
+  stdout_contains: ["Usage: head"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/head/help/short_help_flag.yaml b/tests/scenarios/cmd/head/help/short_help_flag.yaml
new file mode 100644
index 00000000..d128ac81
--- /dev/null
+++ b/tests/scenarios/cmd/head/help/short_help_flag.yaml
@@ -0,0 +1,10 @@
+description: head -h prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    head -h
+expect:
+  stdout_contains: ["Usage: head"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/printf/help/help_flag.yaml b/tests/scenarios/cmd/printf/help/help_flag.yaml
new file mode 100644
index 00000000..5857e3c5
--- /dev/null
+++ b/tests/scenarios/cmd/printf/help/help_flag.yaml
@@ -0,0 +1,10 @@
+description: printf --help prints usage to stdout and exits 2.
+# skip: rshell builtin help output differs from GNU coreutils; also uses exit 2
+skip_assert_against_bash: true
+input:
+  script: |+
+    printf --help
+expect:
+  stdout_contains: ["printf: usage: printf"]
+  stderr: ""
+  exit_code: 2
diff --git a/tests/scenarios/cmd/sed/help/help_flag.yaml b/tests/scenarios/cmd/sed/help/help_flag.yaml
new file mode 100644
index 00000000..fd3fee7e
--- /dev/null
+++ b/tests/scenarios/cmd/sed/help/help_flag.yaml
@@ -0,0 +1,10 @@
+description: sed --help prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    sed --help
+expect:
+  stdout_contains: ["Usage: sed"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/sed/help/short_help_flag.yaml b/tests/scenarios/cmd/sed/help/short_help_flag.yaml
new file mode 100644
index 00000000..962e0e4a
--- /dev/null
+++ b/tests/scenarios/cmd/sed/help/short_help_flag.yaml
@@ -0,0 +1,10 @@
+description: sed -h prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    sed -h
+expect:
+  stdout_contains: ["Usage: sed"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/sort/help/help_flag.yaml b/tests/scenarios/cmd/sort/help/help_flag.yaml
new file mode 100644
index 00000000..2ff23c1e
--- /dev/null
+++ b/tests/scenarios/cmd/sort/help/help_flag.yaml
@@ -0,0 +1,10 @@
+description: sort --help prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    sort --help
+expect:
+  stdout_contains: ["Usage: sort"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/sort/help/short_help_flag.yaml b/tests/scenarios/cmd/sort/help/short_help_flag.yaml
new file mode 100644
index 00000000..e92cc022
--- /dev/null
+++ b/tests/scenarios/cmd/sort/help/short_help_flag.yaml
@@ -0,0 +1,10 @@
+description: sort -h prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    sort -h
+expect:
+  stdout_contains: ["Usage: sort"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/tail/help/help_flag.yaml b/tests/scenarios/cmd/tail/help/help_flag.yaml
new file mode 100644
index 00000000..8d4151c1
--- /dev/null
+++ b/tests/scenarios/cmd/tail/help/help_flag.yaml
@@ -0,0 +1,10 @@
+description: tail --help prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    tail --help
+expect:
+  stdout_contains: ["Usage: tail"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/tail/help/short_help_flag.yaml b/tests/scenarios/cmd/tail/help/short_help_flag.yaml
new file mode 100644
index 00000000..92360858
--- /dev/null
+++ b/tests/scenarios/cmd/tail/help/short_help_flag.yaml
@@ -0,0 +1,10 @@
+description: tail -h prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    tail -h
+expect:
+  stdout_contains: ["Usage: tail"]
+  stderr: ""
+  exit_code: 0
diff --git a/tests/scenarios/cmd/wc/help/help_flag.yaml b/tests/scenarios/cmd/wc/help/help_flag.yaml
new file mode 100644
index 00000000..2ac0cfb0
--- /dev/null
+++ b/tests/scenarios/cmd/wc/help/help_flag.yaml
@@ -0,0 +1,10 @@
+description: wc --help prints usage to stdout and exits 0.
+# skip: rshell builtin help output differs from GNU coreutils
+skip_assert_against_bash: true
+input:
+  script: |+
+    wc --help
+expect:
+  stdout_contains: ["Usage: wc"]
+  stderr: ""
+  exit_code: 0