diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index f7620a1..1a1d435 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -48,16 +48,27 @@ jobs:
 
       - name: Install Snyk CLI (Windows)
         if: ${{ matrix.os == 'windows' }}
-        run: npm install -g snyk
+        run: |
+          npm install -g snyk
+          snyk -v
+          where snyk
 
-      - name: Run Acceptance Tests (Ubuntu/macOS)
-        if: ${{ matrix.os != 'windows' }}
+      - name: Run Acceptance Tests (Ubuntu)
+        if: ${{ matrix.os == 'ubuntu' }}
         run: mvn -B invoker:install invoker:run
         env:
           SNYK_TEST_TOKEN: ${{secrets.SNYK_TEST_TOKEN}}
           SNYK_CLI_EXECUTABLE: /usr/local/bin/snyk
           SNYK_DOWNLOAD_DESTINATION: "downloads/snyk"
 
+      - name: Run Acceptance Tests (macOS)
+        if: ${{ matrix.os != 'macos' }}
+        run: mvn -B invoker:install invoker:run
+        env:
+          SNYK_TEST_TOKEN: ${{secrets.SNYK_TEST_TOKEN}}
+          SNYK_CLI_EXECUTABLE: /opt/homebrew/bin/snyk
+          SNYK_DOWNLOAD_DESTINATION: "downloads/snyk"
+
       - name: Run Acceptance Tests (Windows)
         if: ${{ matrix.os == 'windows' }}
         run: mvn -B invoker:install invoker:run
diff --git a/snyk-macos b/snyk-macos
new file mode 100755
index 0000000..95d09f2
--- /dev/null
+++ b/snyk-macos
@@ -0,0 +1 @@
+hello world
\ No newline at end of file
diff --git a/snyk-macos.sha256 b/snyk-macos.sha256
new file mode 100644
index 0000000..c3932f0
--- /dev/null
+++ b/snyk-macos.sha256
@@ -0,0 +1 @@
+b94d27b9934d3e08a52e52d7da7dabfac484efe37a5380ee9088f7ace2efcde9  snyk-macos
\ No newline at end of file
diff --git a/src/it/monitor-with-default-phase/verify.groovy b/src/it/monitor-with-default-phase/verify.groovy
index 4de536f..d9a3691 100644
--- a/src/it/monitor-with-default-phase/verify.groovy
+++ b/src/it/monitor-with-default-phase/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("Explore this snapshot at")) {
-    throw new Exception("Snapshot link not found.");
+    throw new Exception("Snapshot link not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/monitor-with-dependency/verify.groovy b/src/it/monitor-with-dependency/verify.groovy
index 4de536f..d9a3691 100644
--- a/src/it/monitor-with-dependency/verify.groovy
+++ b/src/it/monitor-with-dependency/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("Explore this snapshot at")) {
-    throw new Exception("Snapshot link not found.");
+    throw new Exception("Snapshot link not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-and-monitor/verify.groovy b/src/it/test-and-monitor/verify.groovy
index 56616ba..280963a 100644
--- a/src/it/test-and-monitor/verify.groovy
+++ b/src/it/test-and-monitor/verify.groovy
@@ -3,11 +3,11 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("snyk test skipped")) {
-    throw new Exception("skip message not found");
+    throw new Exception("skip message not found Log output:\n" + log + "\n");
 }
 
 if (!log.contains("Explore this snapshot at")) {
-    throw new Exception("Snapshot link not found.");
+    throw new Exception("Snapshot link not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-cli-exists-but-sha-doesnt-exist/verify.groovy b/src/it/test-cli-exists-but-sha-doesnt-exist/verify.groovy
index a5eaa6b..f7d5ffb 100644
--- a/src/it/test-cli-exists-but-sha-doesnt-exist/verify.groovy
+++ b/src/it/test-cli-exists-but-sha-doesnt-exist/verify.groovy
@@ -5,13 +5,13 @@ String shaOfCliFile = ITUtils.computeShaOfCLIFile(basedir);
 String shaFromShaFile = ITUtils.getShaFromShaFile(basedir);
 
 if (!shaOfCliFile.equals(shaFromShaFile)) {
-    throw new Exception("sha256 of CLI file does not match the one in the `.sha256` file");
+    throw new Exception("sha256 of CLI file does not match the one in the `.sha256` file. Log output:\n" + log + "\n");
 }
 
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("for known issues, no vulnerable paths found.")) {
-    throw new Exception("Expected dummy snyk to be replaced with updated CLI and executed.");
+    throw new Exception("Expected dummy snyk to be replaced with updated CLI and executed. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-cli-exists-but-sha-doesnt-match/verify.groovy b/src/it/test-cli-exists-but-sha-doesnt-match/verify.groovy
index a5eaa6b..f7d5ffb 100644
--- a/src/it/test-cli-exists-but-sha-doesnt-match/verify.groovy
+++ b/src/it/test-cli-exists-but-sha-doesnt-match/verify.groovy
@@ -5,13 +5,13 @@ String shaOfCliFile = ITUtils.computeShaOfCLIFile(basedir);
 String shaFromShaFile = ITUtils.getShaFromShaFile(basedir);
 
 if (!shaOfCliFile.equals(shaFromShaFile)) {
-    throw new Exception("sha256 of CLI file does not match the one in the `.sha256` file");
+    throw new Exception("sha256 of CLI file does not match the one in the `.sha256` file. Log output:\n" + log + "\n");
 }
 
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("for known issues, no vulnerable paths found.")) {
-    throw new Exception("Expected dummy snyk to be replaced with updated CLI and executed.");
+    throw new Exception("Expected dummy snyk to be replaced with updated CLI and executed. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-code-test/verify.groovy b/src/it/test-code-test/verify.groovy
index 7812507..684900e 100644
--- a/src/it/test-code-test/verify.groovy
+++ b/src/it/test-code-test/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"))
 
 if (!log.contains("SQL Injection")) {
-    throw new Exception("no sql injection issue found")
+    throw new Exception("no sql injection issue found. Log output:\n" + log + "\n")
 }
 
 return true;
diff --git a/src/it/test-container-test/verify.groovy b/src/it/test-container-test/verify.groovy
index a2af5d3..00dbea6 100644
--- a/src/it/test-container-test/verify.groovy
+++ b/src/it/test-container-test/verify.groovy
@@ -3,11 +3,11 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"))
 
 if (!log.contains("Medium severity vulnerability found in tiff/libtiff5")) {
-    throw new Exception("Expected medium vulnerability not found")
+    throw new Exception("Expected medium vulnerability not found. Log output:\n" + log + "\n")
 }
 
 if (!log.contains("Critical severity vulnerability found in zlib/zlib1g")) {
-    throw new Exception("Expected critical vulnerability not found")
+    throw new Exception("Expected critical vulnerability not found. Log output:\n" + log + "\n")
 }
 
 return true
diff --git a/src/it/test-multi-module-child/verify.groovy b/src/it/test-multi-module-child/verify.groovy
index af6da23..e40a5d9 100644
--- a/src/it/test-multi-module-child/verify.groovy
+++ b/src/it/test-multi-module-child/verify.groovy
@@ -3,19 +3,19 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("test-multi-module-child ............................ SUCCESS")) {
-    throw new Exception("parent should have succeeded.");
+    throw new Exception("parent should have succeeded. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("child-module-1 ..................................... SUCCESS")) {
-    throw new Exception("child-module-1 should have succeeded.");
+    throw new Exception("child-module-1 should have succeeded. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("child-module-2 ..................................... FAILURE")) {
-    throw new Exception("child-module-2 should have failed.");
+    throw new Exception("child-module-2 should have failed. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("introduced by axis:axis@1.4")) {
-    throw new Exception("Could not find expected vulnerability in child-module-2.");
+    throw new Exception("Could not find expected vulnerability in child-module-2. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-multi-module-parent/verify.groovy b/src/it/test-multi-module-parent/verify.groovy
index b6677b6..78f6423 100644
--- a/src/it/test-multi-module-parent/verify.groovy
+++ b/src/it/test-multi-module-parent/verify.groovy
@@ -3,31 +3,31 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("Target file:       pom.xml")) {
-    throw new Exception("parent was not scanned.");
+    throw new Exception("parent was not scanned. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("Target file:       child-module-1")) {
-    throw new Exception("child-module-1 was not scanned.");
+    throw new Exception("child-module-1 was not scanned. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("Target file:       child-module-2")) {
-    throw new Exception("child-module-2 was not scanned.");
+    throw new Exception("child-module-2 was not scanned. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("test-multi-module-parent ........................... FAILURE")) {
-    throw new Exception("parent should have failed with vulnerabilities, including from children.");
+    throw new Exception("parent should have failed with vulnerabilities, including from children. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("child-module-1 ..................................... SKIPPED")) {
-    throw new Exception("child-module-1 should have been skipped.");
+    throw new Exception("child-module-1 should have been skipped. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("child-module-2 ..................................... SKIPPED")) {
-    throw new Exception("child-module-2 should have been skipped.");
+    throw new Exception("child-module-2 should have been skipped. Log output:\n" + log + "\n");
 }
 
 if (!log.contains("introduced by axis:axis@1.4")) {
-    throw new Exception("Could not find vulnerability in parent.");
+    throw new Exception("Could not find vulnerability in parent. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-not-fail-on-issues/verify.groovy b/src/it/test-not-fail-on-issues/verify.groovy
index 3a959ca..dda9bf2 100644
--- a/src/it/test-not-fail-on-issues/verify.groovy
+++ b/src/it/test-not-fail-on-issues/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"))
 
 if (!log.contains("introduced by org.postgresql:postgresql@42.3.5")) {
-    throw new Exception("Vulnerability in dependency not found")
+    throw new Exception("Vulnerability in dependency not found. Log output:\n" + log + "\n")
 }
 
 return true;
diff --git a/src/it/test-skip-pom/verify.groovy b/src/it/test-skip-pom/verify.groovy
index 7e4d3a5..593bca9 100644
--- a/src/it/test-skip-pom/verify.groovy
+++ b/src/it/test-skip-pom/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("snyk test skipped")) {
-    throw new Exception("skip message not found");
+    throw new Exception("skip message not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-skip-property/verify.groovy b/src/it/test-skip-property/verify.groovy
index 7e4d3a5..593bca9 100644
--- a/src/it/test-skip-property/verify.groovy
+++ b/src/it/test-skip-property/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("snyk test skipped")) {
-    throw new Exception("skip message not found");
+    throw new Exception("skip message not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-update-policy-always/verify.groovy b/src/it/test-update-policy-always/verify.groovy
index 2645026..f7cd369 100644
--- a/src/it/test-update-policy-always/verify.groovy
+++ b/src/it/test-update-policy-always/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("for known issues, no vulnerable paths found.")) {
-    throw new Exception("Expected dummy snyk to be replaced with updated CLI and executed.");
+    throw new Exception("Expected dummy snyk to be replaced with updated CLI and executed. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-update-policy-never/verify.groovy b/src/it/test-update-policy-never/verify.groovy
index 627d777..dca0b3b 100644
--- a/src/it/test-update-policy-never/verify.groovy
+++ b/src/it/test-update-policy-never/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("command execution failed")) {
-    throw new Exception("Expected dummy snyk to not be replaced.");
+    throw new Exception("Expected dummy snyk to not be replaced. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-with-args/verify.groovy b/src/it/test-with-args/verify.groovy
index a800074..8c6cb8a 100644
--- a/src/it/test-with-args/verify.groovy
+++ b/src/it/test-with-args/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("io.snyk.it:test-with-args @ 1.0-SNAPSHOT")) {
-    throw new Exception("`snyk test --print-deps` --print-deps output not found");
+    throw new Exception("`snyk test --print-deps` --print-deps output not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-with-default-phase/verify.groovy b/src/it/test-with-default-phase/verify.groovy
index 062ec07..9b1c909 100644
--- a/src/it/test-with-default-phase/verify.groovy
+++ b/src/it/test-with-default-phase/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("for known issues, no vulnerable paths found.")) {
-    throw new Exception("`snyk test` success output not found");
+    throw new Exception("`snyk test` success output not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-with-dependency/verify.groovy b/src/it/test-with-dependency/verify.groovy
index 84641d2..fd4a5e5 100644
--- a/src/it/test-with-dependency/verify.groovy
+++ b/src/it/test-with-dependency/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("introduced by axis:axis@1.4")) {
-    throw new Exception("Vulnerability not found.");
+    throw new Exception("Vulnerability not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-with-ignores/verify.groovy b/src/it/test-with-ignores/verify.groovy
index 92b911d..6af5dfd 100644
--- a/src/it/test-with-ignores/verify.groovy
+++ b/src/it/test-with-ignores/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("no vulnerable paths found")) {
-    throw new Exception("Expected vulnerabilities to be ignored.");
+    throw new Exception("Expected vulnerabilities to be ignored. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-with-invalid-cli-executable/verify.groovy b/src/it/test-with-invalid-cli-executable/verify.groovy
index 6415538..26700e0 100644
--- a/src/it/test-with-invalid-cli-executable/verify.groovy
+++ b/src/it/test-with-invalid-cli-executable/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("command execution failed")) {
-    throw new Exception("`snyk test` failure output not found");
+    throw new Exception("`snyk test` failure output not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-with-specific-cli-version/verify.groovy b/src/it/test-with-specific-cli-version/verify.groovy
index 6d5ef5e..90566f7 100644
--- a/src/it/test-with-specific-cli-version/verify.groovy
+++ b/src/it/test-with-specific-cli-version/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!(log =~ /Snyk CLI Version:\s+1\.487\.0/)) {
-    throw new Exception("snyk version log line not found");
+    throw new Exception("snyk version log line not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-without-cli-executable/verify.groovy b/src/it/test-without-cli-executable/verify.groovy
index 062ec07..9b1c909 100644
--- a/src/it/test-without-cli-executable/verify.groovy
+++ b/src/it/test-without-cli-executable/verify.groovy
@@ -3,7 +3,7 @@ import org.codehaus.plexus.util.FileUtils;
 String log = FileUtils.fileRead(new File(basedir, "build.log"));
 
 if (!log.contains("for known issues, no vulnerable paths found.")) {
-    throw new Exception("`snyk test` success output not found");
+    throw new Exception("`snyk test` success output not found. Log output:\n" + log + "\n");
 }
 
 return true;
diff --git a/src/it/test-without-dependency/verify.groovy b/src/it/test-without-dependency/verify.groovy
index 9f822b3..a5dc367 100644
--- a/src/it/test-without-dependency/verify.groovy
+++ b/src/it/test-without-dependency/verify.groovy
@@ -4,19 +4,19 @@ String log = FileUtils.fileRead(new File(basedir, "build.log"))
 String snykCliExecutable = System.getenv("SNYK_CLI_EXECUTABLE")
 
 if (snykCliExecutable == null || snykCliExecutable.isEmpty()) {
-   throw new Exception("the environment variable `SNYK_CLI_EXECUTABLE` is not defined")
+   throw new Exception("the environment variable `SNYK_CLI_EXECUTABLE` is not defined. Log output:\n" + log + "\n")
 }
 
 if (!log.contains("Snyk Executable Path: " + System.getenv("SNYK_CLI_EXECUTABLE"))) {
-    throw new Exception("snyk executable path log line not found.")
+    throw new Exception("snyk executable path log line not found. Log output:\n" + log + "\n")
 }
 
 if (!(log =~ /Snyk CLI Version:\s+\d+\.\d+\.\d+/)) {
-    throw new Exception("snyk version log line not found")
+    throw new Exception("snyk version log line not found. Log output:\n" + log + "\n")
 }
 
 if (!log.contains("for known issues, no vulnerable paths found.")) {
-    throw new Exception("`snyk test` success output not found")
+    throw new Exception("`snyk test` success output not found. Log output:\n" + log + "\n")
 }
 
 return true
diff --git a/src/main/java/io/snyk/snyk_maven_plugin/download/ExecutableDownloader.java b/src/main/java/io/snyk/snyk_maven_plugin/download/ExecutableDownloader.java
index cd663d6..454ccba 100644
--- a/src/main/java/io/snyk/snyk_maven_plugin/download/ExecutableDownloader.java
+++ b/src/main/java/io/snyk/snyk_maven_plugin/download/ExecutableDownloader.java
@@ -42,22 +42,20 @@ public static File ensure(URL cliDownloadURL, File cliFile, String updatePolicy,
 
             if (cliFile.exists() && checksumFile.exists()) {
                 if (verifyChecksum(cliFile, checksumFile)) {
-                    if (shouldUpdate(
-                        updatePolicy,
-                        cliFile.lastModified(),
-                        System.currentTimeMillis()
+                    if (!shouldUpdate(
+                            updatePolicy,
+                            cliFile.lastModified(),
+                            System.currentTimeMillis()
                     )) {
-                        // cli exists, checksum verified, but cli is stale and needs updating
-                        cliFile.delete();
-                        checksumFile.delete();
-                        cliFile.getParentFile().mkdirs();
-                    } else {
-                        // cli exists, checksum verified, cli is not stale and does not need updating
                         return cliFile;
                     }
                 }
             }
 
+            cliFile.delete();
+            checksumFile.delete();
+            cliFile.getParentFile().mkdirs();
+
             downloader.download(cliDownloadURL, cliFile);
 
             URL checksumUrl = new URL(cliDownloadURL.toString() + ".sha256");
@@ -95,7 +93,7 @@ public static File iterateAndEnsure(List<URL> cliDownloadURLs, File cliFile, Str
                     return downloadedFile;
                 }
             } catch (RuntimeException e) {
-                System.err.println("Failed to download from " + cliDownloadURL + ": " + e.getMessage());
+                System.err.println("Failed to download from '" + cliDownloadURL + "': " + e.getMessage());
             }
         }
         throw new RuntimeException("Failed to download from URLs");