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--- a/assets/images/enterprise/legacy-format/README.md
+++ /dev/null
@@ -1,7 +0,0 @@
-### Legacy assets
-
-**Do not add new images to this directory.** This directory will be removed after GHES 3.0 is deprecated.
-
-This directory stores images that were migrated to this repository from AWS S3. These images are not referenced directly in Markdown content. Images in this directory are rendered conditionally using a Unified.js plugin located at [`lib/render-content/plugins/rewite-legacy-asset-paths.js`](lib/render-content/plugins/rewite-legacy-asset-paths.js). When a page is rendered, the plugin checks whether the image referenced in the Markdown content (e.g., /assets/images/foo/bar.png) has a corresponding image in this directory for the version being rendered (e.g., /assets/images/enterprise/legacy-format/<ghes version>/assets/images/foo/bar.png. If a corresponding image does exist in the `legacy-format` directory, the image from the `legacy-format` directory is rendered. If not, the image path referenced in the Markdown is used (e.g., /assets/images/foo/bar.png).
-
-This directory and the `rewrite-legacy-asset-paths` plugin will be removed when GHES 3.0 is deprecated in favor of single-sourcing the images referenced in Markdown, which requires versioning the images in the Markdown content using Liquid conditionals.
\ No newline at end of file
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diff --git a/content/admin/enterprise-management/migrating-from-github-enterprise-1110x-to-2123.md b/content/admin/enterprise-management/migrating-from-github-enterprise-1110x-to-2123.md
index 00638ec3d993..536933512434 100644
--- a/content/admin/enterprise-management/migrating-from-github-enterprise-1110x-to-2123.md
+++ b/content/admin/enterprise-management/migrating-from-github-enterprise-1110x-to-2123.md
@@ -81,7 +81,7 @@ To upgrade to the latest version of {% data variables.product.prodname_enterpris
   ```
 
 12. Return to the new instance's restore status screen to see that the restore completed.
-![Restore complete screen](/assets/images/enterprise/migration/restore-complete-screen.png)
+![Restore complete screen](/assets/images/enterprise/migration/migration-status-complete.png)
 13. Click **Continue to settings** to review and adjust the configuration information and settings that were imported from the previous instance.
 ![Review imported settings](/assets/images/enterprise/migration/migration-status-complete.png)
 14. Click **Save settings**.
diff --git a/content/desktop/contributing-and-collaborating-using-github-desktop/managing-branches.md b/content/desktop/contributing-and-collaborating-using-github-desktop/managing-branches.md
index 879ecd209788..1517a33b7aa5 100644
--- a/content/desktop/contributing-and-collaborating-using-github-desktop/managing-branches.md
+++ b/content/desktop/contributing-and-collaborating-using-github-desktop/managing-branches.md
@@ -30,7 +30,7 @@ You can always create a branch in {% data variables.product.prodname_desktop %}
 {% mac %}
 
 {% data reusables.desktop.click-base-branch-in-drop-down %}
-  ![Drop-down menu to switch your current branch](/assets/images/help/desktop/click-branch-in-drop-down-mac.png)
+  ![Drop-down menu to switch your current branch](/assets/images/help/desktop/select-branch-to-delete.png)
 {% data reusables.desktop.create-new-branch %}
   ![New Branch option in the Branch menu](/assets/images/help/desktop/new-branch-button-mac.png)
 {% data reusables.desktop.name-branch %}
@@ -62,7 +62,7 @@ You can always create a branch in {% data variables.product.prodname_desktop %}
 If you create a branch on {% data variables.product.product_name %}, you'll need to publish the branch to make it available for collaboration on {% data variables.product.prodname_dotcom %}.
 
 1. At the top of the app, click {% octicon "git-branch" aria-label="The branch icon" %} **Current Branch**, then click the branch that you want to publish.
-  ![Drop-down menu to select which branch to publish](/assets/images/help/desktop/click-branch-in-drop-down-mac.png)
+  ![Drop-down menu to select which branch to publish](/assets/images/help/desktop/select-branch-to-delete.png)
 2. Click **Publish branch**.
   ![The Publish branch button](/assets/images/help/desktop/publish-branch-button.png)
 
@@ -77,7 +77,7 @@ You can view and make commits to any of your repository's branches. If you have
 
 {% data reusables.desktop.current-branch-menu %}
 {% data reusables.desktop.switching-between-branches %}
-  ![List of branches in the repository](/assets/images/help/desktop/click-branch-in-drop-down-mac.png)
+  ![List of branches in the repository](/assets/images/help/desktop/select-branch-to-delete.png)
 3. If you have saved, uncommitted changes, choose **Leave my changes** or **Bring my changes**, then click **Switch Branch**.
   ![Switch branch with changes options](/assets/images/help/desktop/stash-changes-options.png)
 
@@ -86,7 +86,7 @@ To access changes you've stashed in another branch, switch back to the branch yo
 
 {% data reusables.desktop.current-branch-menu %}
 {% data reusables.desktop.switching-between-branches %}
-  ![List of branches in the repository](/assets/images/help/desktop/click-branch-in-drop-down-mac.png)
+  ![List of branches in the repository](/assets/images/help/desktop/select-branch-to-delete.png)
 3. In the left sidebar, click **Stashed Changes**.
 ![Stashed changes option](/assets/images/help/desktop/stashed-changes.png)
 4. To delete your stashed changes, click **Discard**, or to use your stashed changes, click **Restore**.
diff --git a/content/desktop/installing-and-configuring-github-desktop/authenticating-to-github.md b/content/desktop/installing-and-configuring-github-desktop/authenticating-to-github.md
index 8bb5f14c5a33..dda5c4f09277 100644
--- a/content/desktop/installing-and-configuring-github-desktop/authenticating-to-github.md
+++ b/content/desktop/installing-and-configuring-github-desktop/authenticating-to-github.md
@@ -24,7 +24,7 @@ Before you authenticate, {% data reusables.desktop.get-an-account %}
 3. To the right of "{% data variables.product.prodname_dotcom_the_website %}," click **Sign In**.
   ![The Sign In button for GitHub](/assets/images/help/desktop/mac-sign-in-github.png)
 4. In the "Sign in" pane, click **Sign in using your browser**. {% data variables.product.prodname_desktop %} will open your default browser.
-  ![The Sign in using your browser link](/assets/images/help/desktop/mac-sign-in-browser.png)
+  ![The Sign in using your browser link](/assets/images/help/desktop/sign-in-browser.png)
 
   {% data reusables.user_settings.password-authentication-deprecation-desktop %}
 
@@ -54,7 +54,7 @@ Before you authenticate, {% data reusables.desktop.get-an-account %}
 3. To the right of "GitHub.com," click **Sign in**.
   ![The Sign In button for GitHub](/assets/images/help/desktop/windows-sign-in-github.png)
 4. In the Sign in pane, click **Sign in using your browser**.
-  ![The Sign in using your browser link](/assets/images/help/desktop/windows-sign-in-browser.png)
+  ![The Sign in using your browser link](/assets/images/help/desktop/sign-in-browser.png)
 
   {% data reusables.user_settings.password-authentication-deprecation-desktop %}
 
diff --git a/content/developers/apps/using-content-attachments.md b/content/developers/apps/using-content-attachments.md
index 3bbe27bf11f4..ed9e9fde07dc 100644
--- a/content/developers/apps/using-content-attachments.md
+++ b/content/developers/apps/using-content-attachments.md
@@ -77,7 +77,7 @@ For more information about creating an installation token, see "[Authenticating
 
 **Step 5.** You'll see the new content attachment appear under the link in a pull request or issue comment:
 
-![Content attached to a reference in an issue](/assets/images/github-apps/github_apps_content_reference_attachment.png)
+![Content attached to a reference in an issue](/assets/images/github-apps/content_reference_attachment.png)
 
 ### Using content attachments in GraphQL
 We provide the `node_id` in the [`content_reference` webhook](/webhooks/event-payloads/#content_reference) event so you can refer to the `createContentAttachment` mutation in the GraphQL API.
@@ -175,4 +175,4 @@ To create a Probot App, follow these steps:
 7. Add a comment to the issue you opened that includes the URL you configured in the `app.yml` file.
 8. Take a look at the issue comment and you'll see an update that looks like this:
 
-   ![Content attached to a reference in an issue](/assets/images/github-apps/github_apps_content_reference_attachment.png)
+   ![Content attached to a reference in an issue](/assets/images/github-apps/content_reference_attachment.png)
diff --git a/content/github/writing-on-github/basic-writing-and-formatting-syntax.md b/content/github/writing-on-github/basic-writing-and-formatting-syntax.md
index 833bf2592f77..5886cb071772 100644
--- a/content/github/writing-on-github/basic-writing-and-formatting-syntax.md
+++ b/content/github/writing-on-github/basic-writing-and-formatting-syntax.md
@@ -197,7 +197,7 @@ For more information, see "[Autolinked references and URLs](/articles/autolinked
 
 Some {% data variables.product.prodname_github_app %}s provide information in {% data variables.product.product_name %} for URLs that link to their registered domains. {% data variables.product.product_name %} renders the information provided by the app under the URL in the body or comment of an issue or pull request.
 
-![Content attachment](/assets/images/help/writing/content-attachment.png)
+![Content attachment](/assets/images/github-apps/content_reference_attachment.png)
 
 To see content attachments, you must have a {% data variables.product.prodname_github_app %} that uses the Content Attachments API installed on the repository.{% if currentVersion == "free-pro-team@latest" %} For more information, see "[Installing an app in your personal account](/articles/installing-an-app-in-your-personal-account)" and "[Installing an app in your organization](/articles/installing-an-app-in-your-organization)."{% endif %}
 
diff --git a/content/insights/installing-and-configuring-github-insights/installing-github-insights.md b/content/insights/installing-and-configuring-github-insights/installing-github-insights.md
index 18658d914df3..60e25e8f1a60 100644
--- a/content/insights/installing-and-configuring-github-insights/installing-github-insights.md
+++ b/content/insights/installing-and-configuring-github-insights/installing-github-insights.md
@@ -33,22 +33,22 @@ To connect {% data variables.product.prodname_insights %} to {% data variables.p
 {% data reusables.organizations.org_settings %}
 {% data reusables.organizations.github-apps-settings-sidebar %}
 5. Click **New {% data variables.product.prodname_github_app %}**.
-  ![New GitHub App button](/assets/images/help/apps/github_apps_new.png)
+  ![New GitHub App button](/assets/images/github-apps/github_apps_new.png)
 6. Under "{% data variables.product.prodname_github_app %} name", type a name for the app. Your app cannot have the same name as an existing user or organization, unless the name is your own user or organization name.
-  ![GitHub App name field](/assets/images/help/apps/github_apps_app_name.png)
+  ![GitHub App name field](/assets/images/github-apps/github_apps_app_name.png)
 7. Under "Homepage URL", type the URL of the application server for {% data variables.product.prodname_insights %}. For more information, see "[System overview for {% data variables.product.prodname_insights %}](/insights/installing-and-configuring-github-insights/system-overview-for-github-insights#requirements-for-running-github-insights)."
-  ![Homepage URL field](/assets/images/help/apps/github_apps_homepage_url.png)
+  ![Homepage URL field](/assets/images/github-apps/github_apps_homepage_url.png)
 8. Under "User authorization callback URL", type the following, replacing `<application-server-url>` with the URL of the application server.
    ```
    <application-server-url>/public/applogin
    ```
-   ![User authorization callback field](/assets/images/help/apps/github_apps_user_authorization.png)
+   ![User authorization callback field](/assets/images/github-apps/github_apps_user_authorization.png)
 9. Under "Setup URL", type `<application-server-url>/public/setup`.
   ![Setup URL field](/assets/images/help/apps/github-apps-setup-url.png)
 9. Under "Webhook URL", type `<application-server-url>/webhooks`.
-   ![Webhook URL field](/assets/images/help/apps/github_apps_webhook_url.png)
+   ![Webhook URL field](/assets/images/github-apps/github_apps_webhook_url.png)
 10. Under "Webhook secret", type a secret, then record the secret for later reference.
-   ![Webhook secret field](/assets/images/help/apps/github_apps_webhook_secret.png)
+   ![Webhook secret field](/assets/images/github-apps/github_apps_webhook_secret.png)
 11. Under "Permissions", use the drop-down menus and configure the following permissions for the app.
     - Repository:
       - Contents: **Read-only**
@@ -71,7 +71,7 @@ To connect {% data variables.product.prodname_insights %} to {% data variables.p
 13. To enable the {% data variables.product.prodname_github_app %} to access data from any user or organization in {% data variables.product.product_location %}, under "Where can this {% data variables.product.prodname_github_app %} be installed?", select **Any account**.
   ![Radio buttons to enable access to any account](/assets/images/help/apps/github_apps_installation_options_any_account.png)
 14. Click **Create {% data variables.product.prodname_github_app %}**.
-  ![Create GitHub App button](/assets/images/help/apps/github_apps_create_github_app.png)
+  ![Create GitHub App button](/assets/images/github-apps/github_apps_create_github_app.png)
 15. Review your app's configuration.
 16. Under "Private keys", click **Generate a private key**.
   ![Generate a private key button](/assets/images/help/apps/generate-private-key.png)
diff --git a/data/reusables/organizations/invite_to_org.md b/data/reusables/organizations/invite_to_org.md
index e20170e43d2c..dd528442c25c 100644
--- a/data/reusables/organizations/invite_to_org.md
+++ b/data/reusables/organizations/invite_to_org.md
@@ -1,4 +1,4 @@
 {% if currentVersion == "free-pro-team@latest" %}1. Type the username, full name, or email address of the person you want to invite and click **Invite**.
   ![Invite member form](/assets/images/help/organizations/org-invite-modal.png){% else %}
 1. Type the username, full name, or email address of the person you want to add and click **Invite**.
-  ![Invite member form](/assets/images/help/organizations/org-invite-modal-ghe.png){% endif %}
+  ![Invite member form](/assets/images/help/organizations/org-invite-modal.png){% endif %}
diff --git a/data/reusables/organizations/security.md b/data/reusables/organizations/security.md
index e8bb0ed5d76d..a29659283cd1 100644
--- a/data/reusables/organizations/security.md
+++ b/data/reusables/organizations/security.md
@@ -1,7 +1,6 @@
 {% if currentVersion == "free-pro-team@latest" or currentVersion ver_gt "enterprise-server@2.21" or currentVersion == "github-ae@latest" %}
 1. In the left sidebar, click **Organization security**.
-  ![Organization security settings](/assets/images/help/organizations/org-security-settings-tab.png)
 {% else %}
 1. In the left sidebar, click **Security**.
- ![Organization security settings](/assets/images/help/organizations/org-settings-security-tab.png)
 {% endif %}
+ ![Organization security settings](/assets/images/help/organizations/org-security-settings-tab.png)
\ No newline at end of file
diff --git a/data/reusables/user-settings/oauth_apps.md b/data/reusables/user-settings/oauth_apps.md
index ad5f4e71d60b..04f120ca6611 100644
--- a/data/reusables/user-settings/oauth_apps.md
+++ b/data/reusables/user-settings/oauth_apps.md
@@ -1,2 +1,2 @@
 1. In the left sidebar, click **OAuth Apps**.
-![OAuth Apps section](/assets/images/settings/oauth_apps_post2dot12.png)
+![OAuth Apps section](/assets/images/settings/developer-settings-oauth-apps.png)