diff --git a/.vscode/launch.json b/.vscode/launch.json
index f5f4b7c351..9e2205f1a2 100644
--- a/.vscode/launch.json
+++ b/.vscode/launch.json
@@ -1,43 +1,35 @@
 {
-    // Use IntelliSense to learn about possible Node.js debug attributes.
-    // Hover to view descriptions of existing attributes.
-    // For more information, visit: https://go.microsoft.com/fwlink/?linkid=830387
-    "version": "0.2.0",
-    "configurations": [
-        {
-            "type": "node",
-            "request": "attach",
-            "name": "Attach to Remote",
-            "address": "localhost",
-            "port": 9229,
-            "localRoot": "${workspaceFolder}"
-        },
-        {
-            "type": "node",
-            "request": "launch",
-            "name": "Launch exports",
-            "preLaunchTask": "compile",
-            "program": "${workspaceRoot}/lib/exports.js",
-            "sourceMaps": true,
-            "outFiles": [
-                "${workspaceRoot}/out/**/*.js"
-            ]
-        },
-        {
-            "type": "node",
-            "request": "launch",
-            "name": "Debug Unit Tests",
-            "program": "${workspaceRoot}/node_modules/.bin/_mocha",
-            "preLaunchTask": "compile",
-            "args": [
-                "--timeout",
-                "999999",
-                "dist/test/unit/**/*.js"
-            ],
-            "sourceMaps": true,
-            "outFiles": [
-                "${workspaceRoot}/dist/**/*.js"
-            ]
-        }
-    ]
-}
\ No newline at end of file
+  // Use IntelliSense to learn about possible Node.js debug attributes.
+  // Hover to view descriptions of existing attributes.
+  // For more information, visit: https://go.microsoft.com/fwlink/?linkid=830387
+  "version": "0.2.0",
+  "configurations": [
+    {
+      "type": "node",
+      "request": "attach",
+      "name": "Attach to Remote",
+      "address": "localhost",
+      "port": 9229,
+      "skipFiles": ["<node_internals>/**/*.js"]
+    },
+    {
+      "type": "node",
+      "request": "launch",
+      "name": "Launch exports",
+      "preLaunchTask": "compile",
+      "program": "${workspaceRoot}/lib/exports.js",
+      "sourceMaps": true,
+      "outFiles": ["${workspaceRoot}/out/**/*.js"]
+    },
+    {
+      "type": "node",
+      "request": "launch",
+      "name": "Debug Unit Tests",
+      "program": "${workspaceRoot}/node_modules/.bin/_mocha",
+      "preLaunchTask": "compile",
+      "args": ["--timeout", "999999", "dist/test/unit/**/*.js"],
+      "sourceMaps": true,
+      "outFiles": ["${workspaceRoot}/dist/**/*.js"]
+    }
+  ]
+}
diff --git a/src/org.ts b/src/org.ts
index 066211daff..2f41482206 100644
--- a/src/org.ts
+++ b/src/org.ts
@@ -16,6 +16,7 @@ import {
   getNumber,
   getString,
   isArray,
+  isBoolean,
   isString,
   JsonArray,
   JsonMap,
@@ -143,7 +144,7 @@ export class Org extends AsyncCreatable<Org.Options> {
         orgForUser = await Org.create({ connection });
       }
 
-      const orgType = (await this.isDevHubOrg()) ? Config.DEFAULT_DEV_HUB_USERNAME : Config.DEFAULT_USERNAME;
+      const orgType = this.isDevHubOrg() ? Config.DEFAULT_DEV_HUB_USERNAME : Config.DEFAULT_USERNAME;
 
       const configInfo: ConfigInfo = await orgForUser.configAggregator.getInfo(orgType);
 
@@ -208,7 +209,7 @@ export class Org extends AsyncCreatable<Org.Options> {
    */
   public async getDevHubOrg(): Promise<Optional<Org>> {
     if (this.isDevHubOrg()) {
-      return Promise.resolve(this);
+      return this;
     } else if (this.getField(Org.Fields.DEV_HUB_USERNAME)) {
       const devHubUsername = ensureString(this.getField(Org.Fields.DEV_HUB_USERNAME));
       return Org.create({
@@ -221,9 +222,49 @@ export class Org extends AsyncCreatable<Org.Options> {
 
   /**
    * Returns `true` if the org is a Dev Hub.
+   *
+   * **Note** This relies on a cached value in the auth file. If that property
+   * is not cached, this method will **always return false even if the org is a
+   * dev hub**. If you need accuracy, use the {@link Org.determineIfDevhub} method.
    */
   public isDevHubOrg(): boolean {
-    return this.getField(Org.Fields.IS_DEV_HUB) as boolean;
+    const isDevHub = this.getField(Org.Fields.IS_DEV_HUB);
+    if (isBoolean(isDevHub)) {
+      return isDevHub;
+    } else {
+      return false;
+    }
+  }
+
+  /**
+   * Returns `true` if the org is a Dev Hub.
+   *
+   * Use a cached value. If the cached value is not set, then check access to the
+   * ScratchOrgInfo object to determine if the org is a dev hub.
+   */
+  public async determineIfDevHubOrg() {
+    if (this.isDevHubOrg()) {
+      return true;
+    }
+
+    const conn = this.getConnection();
+    let isDevHub = false;
+    try {
+      await conn.query('SELECT Id FROM ScratchOrgInfo');
+      isDevHub = true;
+    } catch (err) {
+      /* Not a dev hub */
+    }
+
+    const username = ensure(this.getUsername());
+    const auth = await AuthInfo.create({ username });
+    await auth.save({ isDevHub });
+    AuthInfo.clearCache(username);
+    // Reset the connection with the updated auth file
+    this.connection = await Connection.create({
+      authInfo: await AuthInfo.create({ username })
+    });
+    return isDevHub;
   }
 
   /**
diff --git a/src/testSetup.ts b/src/testSetup.ts
index b783753b39..20e16066f2 100644
--- a/src/testSetup.ts
+++ b/src/testSetup.ts
@@ -293,6 +293,9 @@ const _testSetup = (sinon?: any) => {
       }
       return testContext.fakeConnectionRequest.call(this, request, options);
     });
+
+    // Always start with the default and tests beforeEach or it methods can override it.
+    testContext.fakeConnectionRequest = defaultFakeConnectionRequest;
   });
 
   afterEach(() => {
diff --git a/test/unit/orgTest.ts b/test/unit/orgTest.ts
index 85414442df..78ec215377 100644
--- a/test/unit/orgTest.ts
+++ b/test/unit/orgTest.ts
@@ -623,4 +623,25 @@ describe('Org Tests', () => {
       });
     });
   });
+
+  describe('determineDevHub', () => {
+    it('should return true and cache if dev hub', async () => {
+      const org: Org = await Org.create({ aliasOrUsername: testData.username });
+      $$.fakeConnectionRequest = async (request: AnyJson, options?: AnyJson) => {
+        return { records: [] };
+      };
+      expect(org.isDevHubOrg()).to.be.false;
+      expect(await org.determineIfDevHubOrg()).to.be.true;
+      expect(org.isDevHubOrg()).to.be.true;
+    });
+    it('should return false and cache if dev hub', async () => {
+      const org: Org = await Org.create({ aliasOrUsername: testData.username });
+      $$.fakeConnectionRequest = async (request: AnyJson, options?: AnyJson) => {
+        throw new Error();
+      };
+      expect(org.isDevHubOrg()).to.be.false;
+      expect(await org.determineIfDevHubOrg()).to.be.false;
+      expect(org.isDevHubOrg()).to.be.false;
+    });
+  });
 });