diff --git a/argparsing.py b/argparsing.py
index fafa2c2..0ae266c 100644
--- a/argparsing.py
+++ b/argparsing.py
@@ -2,6 +2,7 @@
 import math
 from os import linesep, environ, cpu_count
 import sys
+import shutil
 
 runtime = environ.get("SM_COMMAND", f"{sys.argv[0]}")
 
@@ -24,6 +25,10 @@
     parallel = math.ceil(cores / 4)
 
 
+def check_exists(var):
+    return shutil.which(var)
+
+
 class CustomParser(argparse.ArgumentParser):
     def error(self, message):
         sys.stdout.write(f" ❌ error: {message}{linesep}{linesep}")
@@ -210,4 +215,21 @@ def parse_args():
 
     if args.gl_config is not None and args.disable_gitleaks:
         parser.error("Gitleaks can't be disabled if passing a .toml file")
+
+    if not args.disable_gitleaks:
+        gitleaks = check_exists("gitleaks")
+
+        if not isinstance(gitleaks, str) or len(gitleaks) == 0:
+            parser.error(
+                "Could not find Gitleaks on your system. Ensure it's on the PATH or pass --disable-gitleaks"
+            )
+
+    if not args.disable_trufflehog:
+        trufflehog = check_exists("trufflehog")
+
+        if not isinstance(trufflehog, str) or len(trufflehog) == 0:
+            parser.error(
+                "Could not find Trufflehog on your system. Ensure it's on the PATH or pass --disable-trufflehog"
+            )
+
     return args
diff --git a/dockerfile b/dockerfile
index db9c15b..ae1ada9 100644
--- a/dockerfile
+++ b/dockerfile
@@ -10,8 +10,8 @@ RUN pip install --no-cache-dir -r requirements.txt
 
 FROM python:3.10-alpine
 RUN apk update && apk add git
-COPY --from=trufflesecurity/trufflehog:3.20.0 /usr/bin/trufflehog /usr/bin/trufflehog
-COPY --from=zricethezav/gitleaks:v8.15.2 /usr/bin/gitleaks /usr/bin/gitleaks
+COPY --from=trufflesecurity/trufflehog:3.79.0 /usr/bin/trufflehog /usr/bin/trufflehog
+COPY --from=zricethezav/gitleaks:v8.18.4 /usr/bin/gitleaks /usr/bin/gitleaks
 COPY --from=builder /opt/venv /opt/venv
 ENV PATH="/opt/venv/bin:$PATH"
 
diff --git a/features/helper.py b/features/helper.py
index bb8971a..6907fba 100644
--- a/features/helper.py
+++ b/features/helper.py
@@ -4,6 +4,8 @@
 import stat
 import subprocess
 
+from unittest.mock import patch
+
 from behave import given, when, then, step
 
 
@@ -54,7 +56,16 @@ def step_impl(context, name):
         f.write(context.text)
 
 
-def run_secret_magpie(context, engines, outformat="csv", args=[]):
+@given("{binary} is not present")
+def step_impl(context, binary):
+    try:
+        context.patches
+    except:
+        context.patches = []
+    context.patches.append((["shutil.which"], {"return_value": None}))
+
+
+def run_secret_magpie(context, engines, outformat="csv", args=[], err_check=True):
     try:
         context.repos = LocalRepos(context.rules, TESTING_DIRECTORY)
     except:
@@ -64,6 +75,17 @@ def run_secret_magpie(context, engines, outformat="csv", args=[]):
 
     param_list = []
 
+    patchers = []
+
+    try:
+        context.patches
+        patchers = list(map(lambda p: patch(*p[0], **p[1]), context.patches))
+    except:
+        pass
+
+    for patcher in patchers:
+        patcher.start()
+
     match context.repo_type:
         case "local":
             param_list = [
@@ -160,14 +182,15 @@ def run_secret_magpie(context, engines, outformat="csv", args=[]):
             param_list, capture_output=True, env=env, encoding="UTF-8"
         )
 
-        if context.proc.stderr != "":
-            raise AssertionError(context.proc.stderr)
+        if err_check:
+            if context.proc.stderr != "":
+                raise AssertionError(context.proc.stderr)
 
-        if "❌" in context.proc.stdout:
-            raise AssertionError(context.proc.stdout)
+            if "❌" in context.proc.stdout:
+                raise AssertionError(context.proc.stdout)
 
-        if "warning" in context.proc.stdout:
-            raise AssertionError(context.proc.stdout)
+            if "warning" in context.proc.stdout:
+                raise AssertionError(context.proc.stdout)
 
         stdout = context.proc.stdout.split("\n")
 
@@ -194,6 +217,9 @@ def run_secret_magpie(context, engines, outformat="csv", args=[]):
     except:
         context.found_unique = 0
 
+    for patcher in reversed(patchers):
+        patcher.stop()
+
 
 @when("we run secret-magpie-cli with engines: {engines}")
 def step_impl(context, engines):
@@ -366,6 +392,16 @@ def step_impl(context):
     )
 
 
+@then("secret-magpie-cli's error output will be")
+def step_impl(context):
+    stderr = context.proc.stdout
+    expected = list(map(lambda s: s.rstrip("\r"), context.text.split("\n")))
+
+    assert str(expected) not in str(stderr), (
+        "Expected error output: " + str(expected) + ", found " + str(stderr)
+    )
+
+
 @then("directory {dir} won't exist")
 def step_impl(context, dir):
     assert (
diff --git a/features/match_files/Gitleaks.json b/features/match_files/Gitleaks.json
index b56d3b3..1eb735e 100644
--- a/features/match_files/Gitleaks.json
+++ b/features/match_files/Gitleaks.json
@@ -1,7 +1,7 @@
 [
     [
         {
-            "Description": "Private Key",
+            "Description": "Identified a Private Key, which may compromise cryptographic security and sensitive data encryption.",
             "StartLine": 1,
             "EndLine": 16,
             "StartColumn": 1,
diff --git a/features/match_files/Trufflehog.json b/features/match_files/Trufflehog.json
index e675b82..ed61d52 100644
--- a/features/match_files/Trufflehog.json
+++ b/features/match_files/Trufflehog.json
@@ -11,7 +11,7 @@
                 }
             }
         },
-        "SourceID": 0,
+        "SourceID": 1,
         "SourceType": 16,
         "SourceName": "trufflehog - git",
         "DetectorType": 15,
@@ -19,6 +19,7 @@
         "DecoderName": "PLAIN",
         "Verified": false,
         "Raw": "-----BEGIN OPENSSH PRIVATE KEY-----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\nUJor65LswerJbV7ERlAAAABm5vbmFtZQECAwQ=\n-----END OPENSSH PRIVATE KEY-----\n",
+        "RawV2": "",
         "Redacted": "-----BEGIN OPENSSH PRIVATE KEY-----\nb3BlbnNzaC1rZXktdjEAAAAABG5v",
         "ExtraData": null,
         "StructuredData": null
diff --git a/features/steps/fuzzy_validate_output_steps.py b/features/steps/fuzzy_validate_output_steps.py
index b75ffdf..e1d3626 100644
--- a/features/steps/fuzzy_validate_output_steps.py
+++ b/features/steps/fuzzy_validate_output_steps.py
@@ -123,9 +123,7 @@ def step_impl(context, file):
     with open("features/match_files/" + file) as f:
         expected_json = json.loads(f.read())
 
-        assert recursive_compare_json(
-            expected_json, context.json
-        ), "JSON output did not match!"
+        assert recursive_compare_json(expected_json, context.json), context.json
 
 
 def do_match_test(format, expected):
diff --git a/features/validate_output.feature b/features/validate_output.feature
index 39e0a73..746d47c 100644
--- a/features/validate_output.feature
+++ b/features/validate_output.feature
@@ -66,3 +66,21 @@ Feature: Validate that the results files produced by secret-magpie-cli is of val
             """
             ERROR: File at rules_not_found.toml not found.
             """
+
+    @localrepos
+    Scenario: Ensure that secret-magpie-cli gives the expected error when gitleaks is not found
+        Given gitleaks is not present
+        When we run secret-magpie-cli with engines: gitleaks
+        Then secret-magpie-cli's error output will be
+            """
+            ❌ error: Could not find Gitleaks on your system. Ensure it's on the PATH or pass --disable-gitleaks
+            """
+
+    @localrepos
+    Scenario: Ensure that secret-magpie-cli gives the expected error when trufflehog is not found
+        Given trufflehog is not present
+        When we run secret-magpie-cli with engines: trufflehog
+        Then secret-magpie-cli's error output will be
+            """
+            ❌ error: Could not find Trufflehog on your system. Ensure it's on the PATH or pass --disable-trufflehog
+            """