diff --git a/packages/cli/CHANGELOG.md b/packages/cli/CHANGELOG.md
index 2a7c9fc4a8..600caf7f87 100644
--- a/packages/cli/CHANGELOG.md
+++ b/packages/cli/CHANGELOG.md
@@ -1,6 +1,10 @@
 # Change Log
 All notable changes to the Zowe CLI package will be documented in this file.
 
+## Recent Changes
+
+- BugFix: Fixed an issue where the `zowe files upload dir-to-uss` command was missing progress bar to track progress of file uploads. [#2344](https://github.com/zowe/zowe-cli/issues/2344)
+
 ## `8.10.3`
 
 - BugFix: The `zowe files copy data-set` command no longer copies all partitioned data set members if a member is specified. [#2402](https://github.com/zowe/zowe-cli/pull/2402)
diff --git a/packages/cli/src/zosfiles/upload/dtu/DirToUSSDir.handler.ts b/packages/cli/src/zosfiles/upload/dtu/DirToUSSDir.handler.ts
index f5c406ac37..44bf308634 100644
--- a/packages/cli/src/zosfiles/upload/dtu/DirToUSSDir.handler.ts
+++ b/packages/cli/src/zosfiles/upload/dtu/DirToUSSDir.handler.ts
@@ -54,12 +54,19 @@ export default class DirToUSSDirHandler extends ZosFilesBaseHandler {
             uploadOptions.filesMap = this.buildFilesMap(commandParameters);
         }
 
-        const uploadApi = commandParameters.arguments.recursive ? Upload.dirToUSSDirRecursive : Upload.dirToUSSDir;
-        const response = await uploadApi.bind(Upload)(session, inputDir, commandParameters.arguments.USSDir, uploadOptions);
+        commandParameters.response.progress.startBar({ task: status });
 
-        const formatMessage = TextUtils.prettyJson(response.apiResponse);
-        commandParameters.response.console.log(formatMessage);
-        return response;
+        try {
+            const uploadApi = commandParameters.arguments.recursive ? Upload.dirToUSSDirRecursive : Upload.dirToUSSDir;
+            const response = await uploadApi.bind(Upload)(session, inputDir, commandParameters.arguments.USSDir, uploadOptions);
+
+            const formatMessage = TextUtils.prettyJson(response.apiResponse);
+            commandParameters.response.console.log(formatMessage);
+
+            return response;
+        } finally {
+            commandParameters.response.progress.endBar();
+        }
     }
 
     private buildFilesMap(commandParameters: IHandlerParameters) {
diff --git a/packages/imperative/CHANGELOG.md b/packages/imperative/CHANGELOG.md
index 6434c10063..375e966ec4 100644
--- a/packages/imperative/CHANGELOG.md
+++ b/packages/imperative/CHANGELOG.md
@@ -5,6 +5,7 @@ All notable changes to the Imperative package will be documented in this file.
 ## Recent Changes
 
 - Enhancement: Added `DeferredPromise` class to Imperative to provide utilities for data synchronization. [#2405](https://github.com/zowe/zowe-cli/pull/2405)
+- 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`
 
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: [],