diff --git a/packages/imperative/CHANGELOG.md b/packages/imperative/CHANGELOG.md
index 490e36fcb8..6bf9028c70 100644
--- a/packages/imperative/CHANGELOG.md
+++ b/packages/imperative/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 All notable changes to the Imperative package will be documented in this file.
 
+## Recent Changes
+
+- BugFix: Fixed a typo in the syntax validation code for positional arguments which caused the validation to never fail. [#2375](https://github.com/zowe/zowe-cli/issues/2375)
+
 ## `8.10.3`
 
 - BugFix: Resolved an issue where extraneous base profiles were created in project configurations when a nested profile property was updated. [#2400](https://github.com/zowe/zowe-cli/pull/2400)
diff --git a/packages/imperative/src/cmd/src/syntax/SyntaxValidator.ts b/packages/imperative/src/cmd/src/syntax/SyntaxValidator.ts
index ea0b0be56b..b95dad3974 100644
--- a/packages/imperative/src/cmd/src/syntax/SyntaxValidator.ts
+++ b/packages/imperative/src/cmd/src/syntax/SyntaxValidator.ts
@@ -226,7 +226,7 @@ export class SyntaxValidator {
                 if (!(commandArguments[positional.name] == null)) {
                     if (positional.regex) {
                         if (commandArguments[positional.name]
-                            .toString().match(new RegExp(positional.regex) == null)) {
+                            .toString().match(new RegExp(positional.regex)) == null) {
                             valid = false;
                             this.positionalParameterInvalid(positional,
                                 commandArguments[positional.name], responseObject);
diff --git a/packages/imperative/src/cmd/src/syntax/__tests__/SyntaxValidator.unit.test.ts b/packages/imperative/src/cmd/src/syntax/__tests__/SyntaxValidator.unit.test.ts
index 58bf12a29c..db03e257c3 100644
--- a/packages/imperative/src/cmd/src/syntax/__tests__/SyntaxValidator.unit.test.ts
+++ b/packages/imperative/src/cmd/src/syntax/__tests__/SyntaxValidator.unit.test.ts
@@ -46,6 +46,9 @@ describe("Imperative should provide advanced syntax validation rules", () => {
         function tryOptions(optionString: string, shouldSucceed: boolean, expectedText?: string[]) {
 
             const options = yargsParser.detailed(optionString, configuration).argv;
+            ValidationTestCommand.positionals?.forEach((p) => {
+                options[p.name] = options._.shift(); // fake out named positionals
+            });
             options._ = ["test", "validation-test"].concat(options._ || []); // fake out command structure
             options[Constants.JSON_OPTION] = true;
             delete options["--"]; // delete extra yargs parse field
@@ -525,6 +528,28 @@ describe("Imperative should provide advanced syntax validation rules", () => {
             expect(svResponse.valid).toEqual(true);
         });
 
+        it("should fail if a positional argument does not match the defined regex", async () => {
+            const invalidPositional = "invalid_value";
+            const regexForPositional = "^\\w+$";
+            ValidationTestCommand.positionals = [{
+                name: invalidPositional,
+                type: "string",
+                description: "Invalid positional",
+                regex: regexForPositional,
+            }];
+
+            return tryOptions.bind(this)(
+                minValidOptions + "inv@lid",
+                false,
+                [
+                    "Invalid format specified for positional option:",
+                    invalidPositional,
+                    "Option must match the following regular expression:",
+                    regexForPositional
+                ]
+            );
+        });
+
         describe("We should be able to validate positional arguments of type 'number'", () => {
             const numberCommand: ICommandDefinition = {
                 name: "gimme-number", aliases: [],