diff --git a/jfrog-tasks-utils/utils.js b/jfrog-tasks-utils/utils.js
index c7aa3b1c..303a8397 100644
--- a/jfrog-tasks-utils/utils.js
+++ b/jfrog-tasks-utils/utils.js
@@ -22,6 +22,8 @@ const jfrogCliReleasesUrl = 'https://releases.jfrog.io/artifactory/jfrog-cli/v2-
 const pipelineRequestedCliVersionEnv = 'JFROG_CLI_PIPELINE_REQUESTED_VERSION_AZURE';
 // The actual JFrog CLI version used in a task.
 const taskSelectedCliVersionEnv = 'JFROG_CLI_TASK_SELECTED_VERSION_AZURE';
+// JFrog CLI version string to get the latest version.
+const jfrogCliReleaseVersionString = '[RELEASE]';
 
 // Maven/Gradle Extractors Env:
 const extractorsRemoteEnv = 'JFROG_CLI_EXTRACTORS_REMOTE';
@@ -97,6 +99,10 @@ function executeCliTask(runTaskFunc, cliVersion, cliDownloadUrl, cliAuthHandlers
         // If CLI version is passed, use it. Otherwise, use requested version from env var if set. Else, default version.
         cliVersion = tl.getVariable(pipelineRequestedCliVersionEnv) || defaultJfrogCliVersion;
     }
+
+    // Convert 'latest' to '[RELEASE]' to get latest jfrog cli version
+    cliVersion = convertLatestVersionToReleaseIfNeeded(cliVersion);
+
     // If unspecified, download from 'releases.jfrog.io' by default.
     if (!cliDownloadUrl) {
         cliDownloadUrl = buildReleasesDownloadUrl(cliVersion);
@@ -174,11 +180,11 @@ function generateDownloadCliErrorMessage(downloadUrl, cliVersion) {
     let errMsg = 'Failed while attempting to download JFrog CLI from ' + downloadUrl + '. ';
     if (downloadUrl === buildReleasesDownloadUrl(cliVersion)) {
         errMsg +=
-            "If this build agent cannot access the internet, you may use the 'Artifactory Tools Installer' task, to download JFrog CLI through an Artifactory repository, which proxies " +
-            buildReleasesDownloadUrl(cliVersion) +
-            '. You ';
+            "\nIf this build agent cannot access the internet, you may use the 'Artifactory Tools Installer' task, to download JFrog CLI through an Artifactory repository, which proxies " +
+            jfrogCliReleasesUrl +
+            '.\nYou ';
     } else {
-        errMsg += 'If the chosen Artifactory Service cannot access the internet, you ';
+        errMsg += '\nIf the chosen Artifactory Service cannot access the internet, \nyou ';
     }
     errMsg += 'may also manually download version ' + cliVersion + ' of JFrog CLI and place it on the agent in the following path: ' + customCliPath;
     return errMsg;
@@ -458,6 +464,11 @@ function addCommonGenericParams(cliCommand, specPath) {
 function logCliVersionAndSetSelected(cliPath) {
     try {
         let detectedVersion = getCliVersion(cliPath);
+        // If the min version allowed is higher than the requested version we will fail the task.
+        if (compareVersions(minCustomCliVersion, detectedVersion) > 0) {
+            tl.setResult(tl.TaskResult.Failed, 'Custom JFrog CLI Version must be at least ' + minCustomCliVersion);
+            return;
+        }
         console.log('JFrog CLI version: ' + detectedVersion);
         tl.setVariable(taskSelectedCliVersionEnv, detectedVersion);
     } catch (ex) {
@@ -496,6 +507,13 @@ function downloadCli(cliDownloadUrl, cliAuthHandlers, cliVersion = defaultJfrogC
         toolLib
             .downloadTool(cliDownloadUrl, null, cliAuthHandlers)
             .then(downloadPath => {
+                // If cliVersion is not a semver ("[RELEASE]" for example), use the executable to get the downloaded version
+                if (!isSemverVersion(cliVersion)) {
+                    if (!isWindows()) {
+                        fs.chmodSync(downloadPath, 0o555);
+                    }
+                    cliVersion = getCliVersion(downloadPath);
+                }
                 toolLib.cacheFile(downloadPath, fileName, jfrogCliToolName, cliVersion).then(cliDir => {
                     let cliPath = path.join(cliDir, fileName);
                     if (!isWindows()) {
@@ -511,6 +529,10 @@ function downloadCli(cliDownloadUrl, cliAuthHandlers, cliVersion = defaultJfrogC
     });
 }
 
+function isSemverVersion(version) {
+    return version && version.split('.').length === 2;
+}
+
 // Compares two versions.
 // Returns 0 if the versions are equal, 1 if version1 is higher and -1 otherwise.
 function compareVersions(version1, version2) {
@@ -804,3 +826,11 @@ function taskDefaultCleanup(cliPath, workDir, serverIdsArray) {
         tl.setResult(tl.TaskResult.Failed, cleanupException);
     }
 }
+
+// Convert latest to "[RELEASE]" to get latest jfrog cli version
+function convertLatestVersionToReleaseIfNeeded(version) {
+    if (version && version.toLowerCase().localeCompare('latest') === 0) {
+        return jfrogCliReleaseVersionString;
+    }
+    return version;
+}
diff --git a/tasks/JFrogCliV2/jfrogCliRun.js b/tasks/JFrogCliV2/jfrogCliRun.js
index 006bcdeb..a2927395 100644
--- a/tasks/JFrogCliV2/jfrogCliRun.js
+++ b/tasks/JFrogCliV2/jfrogCliRun.js
@@ -18,11 +18,6 @@ function RunJfrogCliCommand(RunTaskCbk) {
     }
 
     let cliVersion = tl.getInput('cliVersion', true);
-    // If the min version allowed is higher than the requested version we will fail the task.
-    if (utils.compareVersions(utils.minCustomCliVersion, cliVersion) > 0) {
-        tl.setResult(tl.TaskResult.Failed, 'Custom JFrog CLI Version must be at least ' + utils.minCustomCliVersion);
-        return;
-    }
     utils.executeCliTask(RunTaskCbk, cliVersion);
 }
 
diff --git a/tasks/JFrogCliV2/task.json b/tasks/JFrogCliV2/task.json
index 4b011e8a..86ec20f0 100644
--- a/tasks/JFrogCliV2/task.json
+++ b/tasks/JFrogCliV2/task.json
@@ -42,7 +42,7 @@
             "defaultValue": "$(jfrogCliVersion)",
             "required": true,
             "visibleRule": "useCustomVersion = true",
-            "helpMarkDown": "Specify the version of JFrog CLI to use.\nYou can also set $(jfrogCliVersion)."
+            "helpMarkDown": "Specify the version of JFrog CLI to use.\nYou can also set '$(jfrogCliVersion)' or 'latest'."
         },
         {
             "name": "command",
diff --git a/tasks/JFrogToolsInstaller/toolsInstaller.js b/tasks/JFrogToolsInstaller/toolsInstaller.js
index 0ff1b419..18077094 100644
--- a/tasks/JFrogToolsInstaller/toolsInstaller.js
+++ b/tasks/JFrogToolsInstaller/toolsInstaller.js
@@ -12,11 +12,6 @@ function InstallCliAndExecuteCliTask(RunTaskCbk) {
     // If the variable placeholder was passed (the variable was not set in the pipeline), use the default cli version.
     if (tl.getBoolInput('installCustomVersion') && tl.getInput('cliVersion', true).localeCompare('$(jfrogCliVersion)') !== 0) {
         cliVersion = tl.getInput('cliVersion', true);
-        // If the min version allowed is higher than the requested version we will fail the task.
-        if (utils.compareVersions(utils.minCustomCliVersion, cliVersion) > 0) {
-            tl.setResult(tl.TaskResult.Failed, 'Custom JFrog CLI Version must be at least ' + utils.minCustomCliVersion);
-            return;
-        }
     }
     // Set the requested CLI version env to download it now, and to use in succeeding tasks.
     tl.setVariable(utils.pipelineRequestedCliVersionEnv, cliVersion);