diff --git a/CHANGELOG.md b/CHANGELOG.md
index 69214954da..5092eb9a56 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,4 +1,5 @@
 ### HEAD
+* Fix conditional logic for permalink setup task ([#467](https://github.com/roots/trellis/pull/467))
 * Fix permalink setup during WordPress Install ([#466](https://github.com/roots/trellis/pull/466))
 * Fix deploy pre-flight check for verifying repo ([#463](https://github.com/roots/trellis/pull/463))
 * Add pre-flight checks for common deploy problems ([#459](https://github.com/roots/trellis/pull/459))
diff --git a/README.md b/README.md
index e87f004f82..bab8aee255 100644
--- a/README.md
+++ b/README.md
@@ -122,6 +122,7 @@ For example: configure the sites on your Vagrant development VM by editing `grou
 * `admin_user` - WP admin user name (*development* only, required)
 * `admin_email` - WP admin email address (*development* only, required)
 * `admin_password` - WP admin user password (*development* only, required, in `vault.yml`)
+* `initial_permalink_structure` - permalink structure applied at time of WP install (*development* only, default: `/%postname%/`)
 * `multisite` - hash of multisite options. See the [Multisite docs](https://roots.io/trellis/docs/multisite/).
   * `enabled` - Multisite enabled flag (required, set to `false`)
   * `subdomains` - subdomains option
diff --git a/group_vars/development/wordpress_sites.yml b/group_vars/development/wordpress_sites.yml
index 69b5d4a677..23cc06eb8f 100644
--- a/group_vars/development/wordpress_sites.yml
+++ b/group_vars/development/wordpress_sites.yml
@@ -9,7 +9,7 @@ wordpress_sites:
     admin_user: admin
     # admin_password: (defined in group_vars/development/vault.yml)
     admin_email: admin@example.dev
-    permalink_structure: "/%postname%/"
+    initial_permalink_structure: /%postname%/ # applied only at time of WP install and when `site_install: true`
     multisite:
       enabled: false
       subdomains: false
diff --git a/group_vars/production/wordpress_sites.yml b/group_vars/production/wordpress_sites.yml
index 1f4d8a11d9..510618f038 100644
--- a/group_vars/production/wordpress_sites.yml
+++ b/group_vars/production/wordpress_sites.yml
@@ -7,7 +7,6 @@ wordpress_sites:
     repo: git@github.com:roots/bedrock.git
     branch: master
     # repo_subtree_path: site # relative path to your Bedrock/WP directory in your repo (above) if it is not the root (like the roots-example-project structure)
-    permalink_structure: "/%postname%/"
     multisite:
       enabled: false
       subdomains: false
diff --git a/group_vars/staging/wordpress_sites.yml b/group_vars/staging/wordpress_sites.yml
index a2f79b64da..b6e3703128 100644
--- a/group_vars/staging/wordpress_sites.yml
+++ b/group_vars/staging/wordpress_sites.yml
@@ -7,7 +7,6 @@ wordpress_sites:
     repo: git@github.com:roots/bedrock.git
     branch: master
     # repo_subtree_path: site # relative path to your Bedrock/WP directory in your repo (above) if it is not the root (like the roots-example-project structure)
-    permalink_structure: "/%postname%/"
     multisite:
       enabled: false
       subdomains: false
diff --git a/roles/wordpress-install/tasks/main.yml b/roles/wordpress-install/tasks/main.yml
index ee4fe3dc8b..27af5e42bb 100644
--- a/roles/wordpress-install/tasks/main.yml
+++ b/roles/wordpress-install/tasks/main.yml
@@ -38,26 +38,13 @@
   when: item.value.site_install == True and (item.value.multisite.enabled | default(False) == False)
   changed_when: "'WordPress is already installed.' not in wp_install_results.stdout"
 
-- name: Check Existing Permalink Structure
-  command: wp rewrite list --format=count
-           --allow-root
-           --url="{{ item.value.env.wp_home }}"
-  args:
-    chdir: "{{ www_root }}/{{ item.key }}/current/"
-  register: wp_permalink_check_results
-  with_dict: wordpress_sites
-  when: item.value.site_install and not item.value.multisite.enabled | default(false)
-  changed_when: False
-
 - name: Setup Permalink Structure
-  command: wp rewrite structure {{ item.value.permalink_structure | default("/%postname%/") }}
+  command: wp rewrite structure {{ item.value.initial_permalink_structure | default("/%postname%/") }}
            --allow-root
-           --url="{{ item.value.env.wp_home }}"
   args:
     chdir: "{{ www_root }}/{{ item.key }}/current/"
-  register: wp_permalink_results
   with_dict: wordpress_sites
-  when: "wp_permalink_check_results.changed and 'No rewrite rules' in wp_permalink_check_results.results.0.stderr"
+  when: wp_install_results | changed
 
 - name: Install WP Multisite
   command: wp core multisite-install
@@ -76,7 +63,6 @@
   when: item.value.site_install == True and (item.value.multisite.enabled | default(False) == True)
   changed_when: "'The network already exists.' not in wp_install_results.stdout"
 
-
 - name: Restart HHVM
   service: name=hhvm state=restarted
   when: hhvm | default(False)