diff --git a/addons/core/addon/helpers/doc-url.js b/addons/core/addon/helpers/doc-url.js
index 17109dad3..fcb34852c 100644
--- a/addons/core/addon/helpers/doc-url.js
+++ b/addons/core/addon/helpers/doc-url.js
@@ -23,6 +23,6 @@ export default class extends Helper {
       );
     }
     const path = configuredPath || '';
-    return `${baseURL}${path}`;
+    return path.startsWith('https') ? path : `${baseURL}${path}`;
   }
 }
diff --git a/addons/core/tests/dummy/config/environment.js b/addons/core/tests/dummy/config/environment.js
index d5edfd4cd..f9bc418c3 100644
--- a/addons/core/tests/dummy/config/environment.js
+++ b/addons/core/tests/dummy/config/environment.js
@@ -28,9 +28,11 @@ module.exports = function (environment) {
     companyName: 'Company Name',
 
     documentation: {
-      baseURL: 'https://boundaryproject.io/help/admin-ui',
+      baseURL: 'https://developer.hashicorp.com/boundary',
       topics: {
-        account: '/accounts',
+        account: '/docs/concepts/domain-model/accounts',
+        'host-catalog.aws.region':
+          'https://docs.aws.amazon.com/AmazonRDS/latest/UserGuide/Concepts.RegionsAndAvailabilityZones.html',
       },
     },
 
diff --git a/addons/core/tests/integration/helpers/doc-url-test.js b/addons/core/tests/integration/helpers/doc-url-test.js
index 19a290bf3..6a391606d 100644
--- a/addons/core/tests/integration/helpers/doc-url-test.js
+++ b/addons/core/tests/integration/helpers/doc-url-test.js
@@ -11,11 +11,16 @@ import { hbs } from 'ember-cli-htmlbars';
 module('Integration | Helper | doc-url', function (hooks) {
   setupRenderingTest(hooks);
 
+  let config;
+  let baseURL = hooks.beforeEach(function () {
+    config = this.owner.resolveRegistration('config:environment');
+    baseURL = config.documentation.baseURL;
+  });
+
   test('it renders a URL generated from the documentation config', async function (assert) {
-    const config = this.owner.resolveRegistration('config:environment');
-    const baseURL = config.documentation.baseURL;
     const path = config.documentation.topics.account;
     await render(hbs`{{doc-url 'account'}}`);
+
     assert.ok(baseURL);
     assert.ok(path);
     assert.strictEqual(this.element.textContent.trim(), `${baseURL}${path}`);
@@ -24,9 +29,19 @@ module('Integration | Helper | doc-url', function (hooks) {
   test('it throws an error if the specified documentation path cannot be found', async function (assert) {
     const Helper = this.owner.lookup('helper:doc-url');
     const helper = new Helper(this.owner);
+
     assert.ok(helper.compute(['account']), 'Specified document exists.');
     assert.throws(() => {
       helper.compute(['no.such.doc']);
     }, 'Specified documentation was not found, so the helper threw an error.');
   });
+
+  test('it renders a URL generated from the documentation config without baseURL', async function (assert) {
+    const path = config.documentation.topics['host-catalog.aws.region'];
+    await render(hbs`{{doc-url 'host-catalog.aws.region'}}`);
+
+    assert.ok(baseURL);
+    assert.ok(path);
+    assert.strictEqual(this.element.textContent.trim(), path);
+  });
 });
diff --git a/ui/admin/app/templates/scopes/scope/aliases/alias/index.hbs b/ui/admin/app/templates/scopes/scope/aliases/alias/index.hbs
index ae8d3eca2..80be0597b 100644
--- a/ui/admin/app/templates/scopes/scope/aliases/alias/index.hbs
+++ b/ui/admin/app/templates/scopes/scope/aliases/alias/index.hbs
@@ -10,7 +10,7 @@
   <page.header>
     <h2>
       {{t 'resources.alias.title'}}
-      <DocLink @doc='aliases' @iconSize='large' />
+      <DocLink @doc='alias' @iconSize='large' />
     </h2>
     <p>{{t 'resources.alias.description'}}</p>
     <Hds::Copy::Snippet @color='secondary' @textToCopy={{@model.id}} />
diff --git a/ui/admin/app/templates/scopes/scope/aliases/index.hbs b/ui/admin/app/templates/scopes/scope/aliases/index.hbs
index c468a61f9..7d54aa559 100644
--- a/ui/admin/app/templates/scopes/scope/aliases/index.hbs
+++ b/ui/admin/app/templates/scopes/scope/aliases/index.hbs
@@ -11,7 +11,7 @@
   <page.header>
     <h2>
       {{t 'resources.alias.title_plural'}}
-      <DocLink @doc='aliases' @iconSize='large' />
+      <DocLink @doc='alias' @iconSize='large' />
     </h2>
     <p>{{t 'resources.alias.description'}}</p>
   </page.header>
diff --git a/ui/admin/app/templates/scopes/scope/aliases/new.hbs b/ui/admin/app/templates/scopes/scope/aliases/new.hbs
index 71e8a4edd..7dd39bfd9 100644
--- a/ui/admin/app/templates/scopes/scope/aliases/new.hbs
+++ b/ui/admin/app/templates/scopes/scope/aliases/new.hbs
@@ -17,7 +17,7 @@
   <page.header>
     <h2>
       {{t 'resources.alias.titles.new'}}
-      <DocLink @doc='aliases' @iconSize='large' />
+      <DocLink @doc='alias' @iconSize='large' />
     </h2>
     <p>{{t 'resources.alias.description'}}</p>
 
diff --git a/ui/admin/app/templates/scopes/scope/targets/target/create-alias.hbs b/ui/admin/app/templates/scopes/scope/targets/target/create-alias.hbs
index 8ce97779c..0e20c3840 100644
--- a/ui/admin/app/templates/scopes/scope/targets/target/create-alias.hbs
+++ b/ui/admin/app/templates/scopes/scope/targets/target/create-alias.hbs
@@ -17,7 +17,7 @@
   <page.header>
     <h2>
       {{t 'resources.alias.titles.new'}}
-      <DocLink @doc='aliases' @iconSize='large' />
+      <DocLink @doc='alias' @iconSize='large' />
     </h2>
     <p>{{t 'resources.alias.description'}}</p>
 
diff --git a/ui/admin/app/templates/scopes/scope/targets/target/manage-alias.hbs b/ui/admin/app/templates/scopes/scope/targets/target/manage-alias.hbs
index 92ec2e451..8f48de53b 100644
--- a/ui/admin/app/templates/scopes/scope/targets/target/manage-alias.hbs
+++ b/ui/admin/app/templates/scopes/scope/targets/target/manage-alias.hbs
@@ -15,7 +15,7 @@
   <page.header>
     <h2>
       {{t 'resources.alias.title'}}
-      <DocLink @doc='aliases' @iconSize='large' />
+      <DocLink @doc='alias' @iconSize='large' />
     </h2>
     <p>{{t 'resources.alias.description'}}</p>
     <Hds::Copy::Snippet @color='secondary' @textToCopy={{@model.id}} />
diff --git a/ui/admin/config/environment.js b/ui/admin/config/environment.js
index a621b5915..a99dc7297 100644
--- a/ui/admin/config/environment.js
+++ b/ui/admin/config/environment.js
@@ -56,62 +56,79 @@ module.exports = function (environment) {
     oidcPollingTimeoutSeconds: 1,
 
     documentation: {
-      baseURL: 'https://boundaryproject.io/help/admin-ui',
+      baseURL: 'https://developer.hashicorp.com/boundary',
       topics: {
-        global: '/global',
-        org: '/orgs',
-        'org.new': '/orgs/new',
-        project: '/projects',
-        'project.new': '/projects/new',
-        account: '/accounts',
-        'account.new': '/accounts/new',
-        'auth-method': '/auth-methods',
-        'managed-groups': '/managed-groups',
-        group: '/groups',
-        'group.add-members': '/groups/add-members',
-        'host-catalog': '/host-catalogs',
-        'host-catalog.new': '/host-catalogs/new',
-        'host-catalog.azure': '/dynamic-host-catalogs-on-azure',
-        'host-catalog.aws': '/dynamic-host-catalogs-on-aws',
-        'host-catalog.aws.region': '/dynamic-host-catalogs-on-aws-region',
-        'host-set': '/host-sets',
-        'host-set.new': '/host-sets/new',
-        'host-set.add-hosts': '/host-sets/add-hosts',
-        'host-set.preferred-endpoints': '/host-sets/preferred-endpoints',
-        'host-set.sync-interval-seconds': '/host-sets/sync-interval-seconds',
-        'credential-store': '/credential-stores',
-        'credential-library': '/credential-libraries',
-        credential: '/credentials',
-        host: '/hosts',
-        'host.new': '/hosts/new',
-        role: '/roles',
-        'role.add-principals': '/roles/add-principals',
-        session: '/sessions',
-        target: '/targets',
-        'target.new': '/targets/new',
-        'target.add-host-sources': '/targets/add-host-sets',
-        'target.enable-session-recording': '/targets/enable-session-recording',
-        'target.worker-filters': '/targets/worker-filters',
-        user: '/users',
-        downloads: '/downloads',
-        'getting-started.desktop': '/getting-started/desktop',
-        'api-client.cli': '/api-client/cli',
-        'api-client.api': '/api-client/api',
-        worker: '/workers',
-        'worker.manage-workers': '/workers/manage-workers-on-hcp',
-        'worker-filters': '/worker-filters',
-        'storage-bucket': '/storage-buckets',
-        'storage-bucket.new': '/storage-buckets/new',
-        'storage-bucket.worker-filter': '/storage-buckets/worker-filter',
+        global: '/docs/concepts/domain-model/scopes#global',
+        org: '/docs/concepts/domain-model/scopes#organizations',
+        'org.new': '/docs/common-workflows/manage-scopes',
+        project: '/docs/concepts/domain-model/scopes#projects',
+        'project.new': '/docs/common-workflows/manage-scopes',
+        account: '/docs/concepts/domain-model/accounts',
+        'account.new':
+          '/tutorials/oss-administration/oss-manage-users-groups#create-an-account',
+        'auth-method': '/docs/concepts/domain-model/auth-methods',
+        'managed-groups': '/docs/concepts/domain-model/managed-groups',
+        group: '/docs/concepts/domain-model/groups',
+        'group.add-members':
+          '/tutorials/oss-administration/oss-manage-users-groups#create-a-group',
+        'host-catalog': '/docs/concepts/domain-model/host-catalogs',
+        'host-catalog.new': '/docs/common-workflows/manage-targets',
+        'host-catalog.azure': '/docs/concepts/host-discovery/azure',
+        'host-catalog.aws': '/docs/concepts/host-discovery/aws',
+        'host-catalog.aws.region':
+          'https://docs.aws.amazon.com/AmazonRDS/latest/UserGuide/Concepts.RegionsAndAvailabilityZones.html',
+        'host-set': '/docs/concepts/domain-model/host-sets',
+        'host-set.new':
+          '/docs/common-workflows/manage-targets#define-a-host-set',
+        'host-set.add-hosts': '/docs/concepts/domain-model/hosts',
+        'host-set.preferred-endpoints':
+          '/docs/concepts/domain-model/host-sets#preferred_endpoints',
+        'host-set.sync-interval-seconds':
+          '/docs/concepts/domain-model/host-sets#sync_interval_seconds',
+        'credential-store': '/docs/concepts/domain-model/credential-stores',
+        'credential-library':
+          '/docs/concepts/domain-model/credential-libraries',
+        credential: '/docs/concepts/domain-model/credentials',
+        host: '/docs/concepts/domain-model/hosts',
+        'host.new': '/docs/common-workflows/manage-targets#define-a-host',
+        role: '/docs/concepts/domain-model/roles',
+        'role.add-principals':
+          '/tutorials/oss-administration/oss-manage-roles#create-a-role',
+        session: '/docs/concepts/domain-model/sessions',
+        target: '/docs/concepts/domain-model/targets',
+        'target.new': '/docs/common-workflows/manage-targets',
+        'target.add-host-sources': '/docs/concepts/domain-model/host-sets',
+        'target.enable-session-recording':
+          '/docs/configuration/session-recording/enable-session-recording',
+        'target.worker-filters':
+          '/docs/concepts/filtering/worker-tags#worker-filtering',
+        user: '/docs/concepts/domain-model/users',
+        downloads: '/install',
+        'getting-started.desktop':
+          '/tutorials/oss-getting-started/oss-getting-started-desktop-app',
+        'api-client.cli': '/docs/commands',
+        'api-client.api': '/docs/api-clients/api',
+        worker: '/docs/configuration/worker',
+        'worker.manage-workers':
+          '/tutorials/hcp-administration/hcp-manage-workers',
+        'worker-filters':
+          '/docs/concepts/domain-model/credential-stores#worker_filter',
+        'storage-bucket': '/docs/concepts/domain-model/storage-buckets',
+        'storage-bucket.new':
+          '/docs/configuration/session-recording/create-storage-bucket',
+        'storage-bucket.worker-filter':
+          '/docs/concepts/domain-model/storage-buckets#worker_filter',
         'storage-bucket.disable-credential-rotation':
-          '/storage-buckets/disable-credential-rotation',
-        'session-recording': '/session-recordings',
+          '/docs/concepts/domain-model/storage-buckets#disable_credential_rotation',
+        'session-recording': '/docs/concepts/domain-model/session-recordings',
         'session-recording.retrieve-lost-session-recordings':
-          '/session-recordings/retrieve-lost-session-recordings',
-        'storage-policy': '/storage-policy',
-        'storage-policy.new': '/storage-policy/new',
-        'storage-policy.update': '/storage-policy/update',
-        aliases: '/aliases',
+          '/docs/operations/manage-recorded-sessions',
+        'storage-policy': '/docs/concepts/domain-model/storage-policy',
+        'storage-policy.new':
+          '/docs/configuration/session-recording/configure-storage-policy',
+        'storage-policy.update':
+          '/docs/configuration/session-recording/update-storage-policy',
+        alias: '/docs/concepts/aliases',
       },
     },
 
diff --git a/ui/admin/tests/acceptance/credential-store/create-test.js b/ui/admin/tests/acceptance/credential-store/create-test.js
index 0e2c72c4a..881861ff8 100644
--- a/ui/admin/tests/acceptance/credential-store/create-test.js
+++ b/ui/admin/tests/acceptance/credential-store/create-test.js
@@ -145,7 +145,7 @@ module('Acceptance | credential-stores | create', function (hooks) {
     await visit(urls.newCredentialStore);
     assert.ok(
       find(
-        `[href="https://boundaryproject.io/help/admin-ui/credential-stores"]`,
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/credential-stores"]`,
       ),
     );
   });
diff --git a/ui/admin/tests/acceptance/credential-store/credentials/read-test.js b/ui/admin/tests/acceptance/credential-store/credentials/read-test.js
index 34b4e7f34..6fe5d8c68 100644
--- a/ui/admin/tests/acceptance/credential-store/credentials/read-test.js
+++ b/ui/admin/tests/acceptance/credential-store/credentials/read-test.js
@@ -153,7 +153,9 @@ module('Acceptance | credential-stores | credentials | read', function (hooks) {
   test('Users can link to docs page for credential', async function (assert) {
     await visit(urls.usernamePasswordCredential);
     assert.ok(
-      find(`[href="https://boundaryproject.io/help/admin-ui/credentials"]`),
+      find(
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/credentials"]`,
+      ),
     );
   });
 
diff --git a/ui/admin/tests/acceptance/credential-store/list-test.js b/ui/admin/tests/acceptance/credential-store/list-test.js
index a45b04113..e0ada1121 100644
--- a/ui/admin/tests/acceptance/credential-store/list-test.js
+++ b/ui/admin/tests/acceptance/credential-store/list-test.js
@@ -130,7 +130,7 @@ module('Acceptance | credential-stores | list', function (hooks) {
 
     assert
       .dom(
-        `[href="https://boundaryproject.io/help/admin-ui/credential-stores"]`,
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/credential-stores"]`,
       )
       .exists();
   });
diff --git a/ui/admin/tests/acceptance/credential-store/read-test.js b/ui/admin/tests/acceptance/credential-store/read-test.js
index 6a941eeed..0ef319643 100644
--- a/ui/admin/tests/acceptance/credential-store/read-test.js
+++ b/ui/admin/tests/acceptance/credential-store/read-test.js
@@ -133,7 +133,7 @@ module('Acceptance | credential-stores | read', function (hooks) {
 
     assert
       .dom(
-        `[href="https://boundaryproject.io/help/admin-ui/credential-stores"]`,
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/credential-stores"]`,
       )
       .exists();
   });
diff --git a/ui/admin/tests/acceptance/host-catalogs/host-sets/read-test.js b/ui/admin/tests/acceptance/host-catalogs/host-sets/read-test.js
index 7fdacc2c8..f7ec67d3f 100644
--- a/ui/admin/tests/acceptance/host-catalogs/host-sets/read-test.js
+++ b/ui/admin/tests/acceptance/host-catalogs/host-sets/read-test.js
@@ -105,7 +105,9 @@ module('Acceptance | host-catalogs | host-sets | read', function (hooks) {
     await click(`[href="${urls.hostSet}"]`);
 
     assert
-      .dom(`[href="https://boundaryproject.io/help/admin-ui/host-sets"]`)
+      .dom(
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/host-sets"]`,
+      )
       .exists();
   });
 
diff --git a/ui/admin/tests/acceptance/host-catalogs/hosts/read-test.js b/ui/admin/tests/acceptance/host-catalogs/hosts/read-test.js
index f7342012f..81cc9ae9f 100644
--- a/ui/admin/tests/acceptance/host-catalogs/hosts/read-test.js
+++ b/ui/admin/tests/acceptance/host-catalogs/hosts/read-test.js
@@ -105,7 +105,9 @@ module('Acceptance | host-catalogs | hosts | read', function (hooks) {
     await click(`[href="${urls.host}"]`);
 
     assert
-      .dom(`[href="https://boundaryproject.io/help/admin-ui/hosts"]`)
+      .dom(
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/hosts"]`,
+      )
       .exists();
   });
 
diff --git a/ui/admin/tests/acceptance/host-catalogs/read-test.js b/ui/admin/tests/acceptance/host-catalogs/read-test.js
index e8f0fc557..74338f5d5 100644
--- a/ui/admin/tests/acceptance/host-catalogs/read-test.js
+++ b/ui/admin/tests/acceptance/host-catalogs/read-test.js
@@ -99,7 +99,9 @@ module('Acceptance | host-catalogs | read', function (hooks) {
     await click(`[href="${urls.hostCatalogs}"]`);
 
     assert
-      .dom(`[href="https://boundaryproject.io/help/admin-ui/host-catalogs"]`)
+      .dom(
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/host-catalogs"]`,
+      )
       .exists();
   });
 
diff --git a/ui/admin/tests/acceptance/sessions/list-test.js b/ui/admin/tests/acceptance/sessions/list-test.js
index c27054d8d..4c776390d 100644
--- a/ui/admin/tests/acceptance/sessions/list-test.js
+++ b/ui/admin/tests/acceptance/sessions/list-test.js
@@ -188,7 +188,9 @@ module('Acceptance | sessions | list', function (hooks) {
     await click(`[href="${urls.sessions}"]`);
 
     assert
-      .dom(`[href="https://boundaryproject.io/help/admin-ui/sessions"]`)
+      .dom(
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/sessions"]`,
+      )
       .exists();
   });
 
diff --git a/ui/admin/tests/acceptance/targets/read-test.js b/ui/admin/tests/acceptance/targets/read-test.js
index fe7654d94..8510e69cd 100644
--- a/ui/admin/tests/acceptance/targets/read-test.js
+++ b/ui/admin/tests/acceptance/targets/read-test.js
@@ -198,7 +198,9 @@ module('Acceptance | targets | read', function (hooks) {
     await click(`[href="${urls.targets}"]`);
 
     assert
-      .dom(`[href="https://boundaryproject.io/help/admin-ui/targets"]`)
+      .dom(
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/targets"]`,
+      )
       .exists();
   });
 
diff --git a/ui/admin/tests/acceptance/users/read-test.js b/ui/admin/tests/acceptance/users/read-test.js
index 4f8c5eb08..62e197f3a 100644
--- a/ui/admin/tests/acceptance/users/read-test.js
+++ b/ui/admin/tests/acceptance/users/read-test.js
@@ -85,7 +85,9 @@ module('Acceptance | users | read', function (hooks) {
     await click(`[href="${urls.users}"]`);
 
     assert
-      .dom(`[href="https://boundaryproject.io/help/admin-ui/users"]`)
+      .dom(
+        `[href="https://developer.hashicorp.com/boundary/docs/concepts/domain-model/users"]`,
+      )
       .exists();
   });
 
diff --git a/ui/desktop/config/environment.js b/ui/desktop/config/environment.js
index 208210992..bb1024e22 100644
--- a/ui/desktop/config/environment.js
+++ b/ui/desktop/config/environment.js
@@ -47,10 +47,12 @@ module.exports = function (environment) {
     oidcPollingTimeoutSeconds: 1,
 
     documentation: {
-      baseURL: 'https://boundaryproject.io/help/desktop',
+      baseURL: 'https://developer.hashicorp.com/boundary',
       topics: {
-        targets: '/targets',
-        sessions: '/sessions',
+        targets:
+          '/tutorials/oss-getting-started/oss-getting-started-desktop-app#connect',
+        sessions:
+          '/tutorials/oss-getting-started/oss-getting-started-desktop-app#connect',
       },
     },
 
diff --git a/ui/desktop/electron-app/src/index.js b/ui/desktop/electron-app/src/index.js
index 547914841..d9112ff55 100644
--- a/ui/desktop/electron-app/src/index.js
+++ b/ui/desktop/electron-app/src/index.js
@@ -142,12 +142,12 @@ const createWindow = (partition, closeWindowCB) => {
   });
 
   // Opens external links in the host default browser.
-  // We allow boundaryproject.io domain to open on external window (for now)
+  // We allow developer.hashicorp.com domain to open on external window
   // and releases.hashicorp.com domain to download the desktop app or
   // link to the release page for the desktop app.
   browserWindow.webContents.setWindowOpenHandler(({ url }) => {
     if (
-      url.startsWith('https://boundaryproject.io/') ||
+      url.startsWith('https://developer.hashicorp.com/') ||
       url.startsWith('https://releases.hashicorp.com/boundary-desktop/')
     ) {
       shell.openExternal(url);