diff --git a/src/api/IBMi.ts b/src/api/IBMi.ts
index 27fdee307..2ec8228b4 100644
--- a/src/api/IBMi.ts
+++ b/src/api/IBMi.ts
@@ -182,7 +182,10 @@ export default class IBMi {
           });
           const delayedOperations: Function[] = [...onConnectedOperations];
 
-          await this.client.connect(connectionObject as node_ssh.Config);
+          await this.client.connect({
+            ...connectionObject,
+            privateKeyPath: connectionObject.privateKeyPath ? Tools.resolvePath(connectionObject.privateKeyPath) : undefined
+          } as node_ssh.Config);
 
           cancelToken.onCancellationRequested(() => {
             this.end();
@@ -1504,7 +1507,7 @@ export default class IBMi {
     return this.componentManager.get<T>(name, ignoreState);
   }
 
-  getComponentStates(){
+  getComponentStates() {
     return this.componentManager.getState();
   }
 
diff --git a/src/api/IBMiContent.ts b/src/api/IBMiContent.ts
index 6c6871308..4efed6a1d 100644
--- a/src/api/IBMiContent.ts
+++ b/src/api/IBMiContent.ts
@@ -957,15 +957,15 @@ export default class IBMiContent {
       target = localPath;
     }
 
-    target = IBMi.escapeForShell(target);
-
     let result: CommandResult;
 
     if (assumeMember) {
+      target = IBMi.escapeForShell(target);
       result = await this.ibmi.sendQsh({ command: `${this.ibmi.remoteFeatures.attr} -p ${target} ${operands.join(" ")}`});
     } else {
+      target = Tools.escapePath(target, true);
       // Take {DOES_THIS_WORK: `YESITDOES`} away, and all of a sudden names with # aren't found.
-      result = await this.ibmi.sendCommand({ command: `${this.ibmi.remoteFeatures.attr} -p ${target} ${operands.join(" ")}`, env: {DOES_THIS_WORK: `YESITDOES`}});
+      result = await this.ibmi.sendCommand({ command: `${this.ibmi.remoteFeatures.attr} -p "${target}" ${operands.join(" ")}`, env: {DOES_THIS_WORK: `YESITDOES`}});
     }
 
     if (result.code === 0) {
diff --git a/src/api/Tools.ts b/src/api/Tools.ts
index 6b68d3402..7c760ba1b 100644
--- a/src/api/Tools.ts
+++ b/src/api/Tools.ts
@@ -1,5 +1,6 @@
 import Crypto from 'crypto';
 import { readFileSync } from "fs";
+import os from "os";
 import path from "path";
 import vscode from "vscode";
 import { IBMiMessage, IBMiMessages, QsysPath } from '../typings';
@@ -401,14 +402,14 @@ export namespace Tools {
 
   export function assumeType(str: string) {
     if (str.trim().length === 0) return ``;
-    
+
     // The number is already generated on the server.
     // So, we assume that if the string starts with a 0, it is a string.
     if (/^0.+/.test(str) || str.length > 10) {
       return str
     }
     const number = Number(str);
-    if(isNaN(number)){
+    if (isNaN(number)) {
       return str;
     }
     return number;
@@ -463,4 +464,33 @@ export namespace Tools {
     }
     return 0;
   }
+
+  /**
+   * Transforms a file path into an OS agnostic path.
+   * - Replaces full home directory path by ~
+   * - Replaces all \ into / on Windows
+   * 
+   * @param filePath 
+   * @returns 
+   */
+  export function normalizePath(filePath: string) {
+    //Test path in lowercase since os.homedir doesn't always has the same case as filePath on Windows
+    if(filePath.toLowerCase().startsWith(os.homedir().toLowerCase())){
+      filePath = path.join(`~`, filePath.substring(os.homedir().length));
+    }
+    
+    return process.platform === "win32" ? filePath.replaceAll('\\', '/') : filePath;
+  }
+
+  /**
+   * Transforms a normalized path into an OS specific path.
+   * - Replaces ~ with the current home directory
+   * - Changes all / to \ on Windows
+   * @param path 
+   * @returns 
+   */
+  export function resolvePath(path: string) {
+    path = path.replace("~", os.homedir());
+    return process.platform === "win32" ? path.replaceAll('/', '\\') : path;
+  }
 }
\ No newline at end of file
diff --git a/src/extension.ts b/src/extension.ts
index c383bb514..7f204a824 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -8,7 +8,7 @@ import { CustomUI } from "./api/CustomUI";
 import { instance, loadAllofExtension } from './instantiate';
 
 import { CompileTools } from "./api/CompileTools";
-import { ConnectionConfiguration, ConnectionManager, GlobalConfiguration, onCodeForIBMiConfigurationChange } from "./api/Configuration";
+import { ConnectionConfiguration, ConnectionManager, onCodeForIBMiConfigurationChange } from "./api/Configuration";
 import IBMi from "./api/IBMi";
 import { GlobalStorage } from "./api/Storage";
 import { Tools } from "./api/Tools";
@@ -142,38 +142,6 @@ export async function activate(context: ExtensionContext): Promise<CodeForIBMi>
   };
 }
 
-async function fixLoginSettings() {
-  const connections = (GlobalConfiguration.get<ConnectionData[]>(`connections`) || []);
-  let update = false;
-  for (const connection of connections) {
-    //privateKey was used to hold privateKeyPath 
-    if ('privateKey' in connection) {
-      const privateKey = connection["privateKey"] as string;
-      if (privateKey) {
-        connection.privateKeyPath = privateKey;
-      }
-      delete connection["privateKey"];
-      update = true;
-    }
-
-    //An empty privateKeyPath will crash the connection
-    if (!connection.privateKeyPath?.trim()) {
-      connection.privateKeyPath = undefined;
-      update = true;
-    }
-
-    //buttons were added by the login settings page
-    if (`buttons` in connection) {
-      delete connection["buttons"];
-      update = true;
-    }
-  }
-
-  if (update) {
-    await GlobalConfiguration.set(`connections`, connections);
-  }
-}
-
 // this method is called when your extension is deactivated
 export async function deactivate() {
   await commands.executeCommand(`code-for-ibmi.disconnect`, true);
diff --git a/src/testing/encoding.ts b/src/testing/encoding.ts
index e89fe1327..bd486ad35 100644
--- a/src/testing/encoding.ts
+++ b/src/testing/encoding.ts
@@ -91,6 +91,44 @@ export const EncodingSuite: TestSuite = {
         assert.ok(result?.length);
       }
     },
+    {
+      name: `Files and directories with spaces`, test: async () => {
+        const connection = instance.getConnection()!;
+
+        await connection.withTempDirectory(async tempDir => {
+          const dirName = `hello world`;
+          const dirWithSpace = path.posix.join(tempDir, dirName);
+          const fileName = `hello world.txt`;
+          const nameWithSpace = path.posix.join(dirWithSpace, fileName);
+
+          await connection.sendCommand({command: `mkdir -p "${dirWithSpace}"`});
+          await connection.content.createStreamFile(nameWithSpace);
+
+          // Resolve and get attributes
+          const resolved = await connection.content.streamfileResolve([fileName], [tempDir, dirWithSpace]);
+          assert.strictEqual(resolved, nameWithSpace);
+
+          const attributes = await connection.content.getAttributes(resolved, `CCSID`);
+          assert.ok(attributes);
+
+          // Write and read the files
+          const uri = Uri.from({scheme: `streamfile`, path: nameWithSpace});
+          await workspace.fs.writeFile(uri, Buffer.from(`Hello world`, `utf8`));
+
+          const streamfileContents = await workspace.fs.readFile(uri);
+          assert.ok(streamfileContents.toString().includes(`Hello world`));
+
+          // List files
+          const files = await connection.content.getFileList(tempDir);
+          assert.strictEqual(files.length, 1);
+          assert.ok(files.some(f => f.name === dirName && f.path === dirWithSpace));
+
+          const files2 = await connection.content.getFileList(dirWithSpace);
+          assert.strictEqual(files2.length, 1);
+          assert.ok(files2.some(f => f.name === fileName && f.path === nameWithSpace));
+        });
+      }
+    },
     {
       name: `Run variants through shells`, test: async () => {
         const connection = instance.getConnection();
diff --git a/src/typings.ts b/src/typings.ts
index 381b4e6cb..753808116 100644
--- a/src/typings.ts
+++ b/src/typings.ts
@@ -83,7 +83,6 @@ export interface ConnectionData {
   port: number;
   username: string;
   password?: string;
-  privateKey?: string;
   privateKeyPath?: string;
   keepaliveInterval?: number;
 }
diff --git a/src/webviews/login/index.ts b/src/webviews/login/index.ts
index 2c6943541..137eba7c5 100644
--- a/src/webviews/login/index.ts
+++ b/src/webviews/login/index.ts
@@ -2,6 +2,7 @@ import vscode, { l10n, ThemeIcon } from "vscode";
 import { ConnectionConfiguration, ConnectionManager } from "../../api/Configuration";
 import { CustomUI, Section } from "../../api/CustomUI";
 import IBMi from "../../api/IBMi";
+import { Tools } from "../../api/Tools";
 import { disconnect, instance } from "../../instantiate";
 import { ConnectionData } from '../../typings';
 
@@ -54,7 +55,7 @@ export class Login {
       page.panel.dispose();
 
       data.port = Number(data.port);
-      data.privateKeyPath = data.privateKeyPath?.trim() ? data.privateKeyPath : undefined;
+      data.privateKeyPath = data.privateKeyPath?.trim() ? Tools.normalizePath(data.privateKeyPath) : undefined;
       if (data.name) {
         const existingConnection = ConnectionManager.getByName(data.name);
 
diff --git a/src/webviews/settings/index.ts b/src/webviews/settings/index.ts
index 9f3e2083e..124753276 100644
--- a/src/webviews/settings/index.ts
+++ b/src/webviews/settings/index.ts
@@ -1,3 +1,4 @@
+import { existsSync } from "fs";
 import vscode from "vscode";
 import { ConnectionConfiguration, ConnectionManager, GlobalConfiguration } from "../../api/Configuration";
 import { ComplexTab, CustomUI, Section } from "../../api/CustomUI";
@@ -352,14 +353,15 @@ export class SettingsUI {
           if (connection) {
             const storedPassword = await ConnectionManager.getStoredPassword(context, name);
             let { data: stored, index } = connection;
-
+            const privateKeyPath = stored.privateKeyPath ? Tools.resolvePath(stored.privateKeyPath) : undefined;
+            const privateKeyWarning = !privateKeyPath || existsSync(privateKeyPath) ? "" : "<b>⚠️ This private key doesn't exist on this system! ⚠️</b></br></br>";
             const ui = new CustomUI()
               .addInput(`host`, vscode.l10n.t(`Host or IP Address`), undefined, { default: stored.host, minlength: 1 })
               .addInput(`port`, vscode.l10n.t(`Port (SSH)`), undefined, { default: String(stored.port), minlength: 1, maxlength: 5, regexTest: `^\\d+$` })
               .addInput(`username`, vscode.l10n.t(`Username`), undefined, { default: stored.username, minlength: 1 })
               .addParagraph(vscode.l10n.t(`Only provide either the password or a private key - not both.`))
               .addPassword(`password`, `${vscode.l10n.t(`Password`)}${storedPassword ? ` (${vscode.l10n.t(`stored`)})` : ``}`, vscode.l10n.t("Only provide a password if you want to update an existing one or set a new one."))
-              .addFile(`privateKeyPath`, `${vscode.l10n.t(`Private Key`)}${stored.privateKeyPath ? ` (${vscode.l10n.t(`Private Key`)}: ${stored.privateKeyPath})` : ``}`, vscode.l10n.t("Only provide a private key if you want to update from the existing one or set one.") + '<br />' + vscode.l10n.t("OpenSSH, RFC4716 and PPK formats are supported."))
+              .addFile(`privateKeyPath`, `${vscode.l10n.t(`Private Key`)}${privateKeyPath ? ` (${vscode.l10n.t(`Private Key`)}: ${privateKeyPath})` : ``}`, privateKeyWarning + vscode.l10n.t("Only provide a private key if you want to update from the existing one or set one.") + '<br />' + vscode.l10n.t("OpenSSH, RFC4716 and PPK formats are supported."))
               .addButtons(
                 { id: `submitButton`, label: vscode.l10n.t(`Save`), requiresValidation: true },
                 { id: `removeAuth`, label: vscode.l10n.t(`Remove auth methods`) }
@@ -393,6 +395,7 @@ export class SettingsUI {
                       // If no password was entered, but a keypath exists
                       // then remove the password from the data and
                       // use the keypath instead
+                      data.privateKeyPath = Tools.normalizePath(data.privateKeyPath);
                       await ConnectionManager.deleteStoredPassword(context, name);
                       vscode.window.showInformationMessage(vscode.l10n.t(`Private key updated and will be used for "{0}".`, name));
                     }