diff --git a/deckhand/engine/schemas/base_schema.yaml b/deckhand/engine/schemas/base_schema.yaml
index 93830034..49b3a401 100644
--- a/deckhand/engine/schemas/base_schema.yaml
+++ b/deckhand/engine/schemas/base_schema.yaml
@@ -35,6 +35,16 @@ data:
         actions:
           required:
             - parentSelector
+    substitution_dest:
+      type: object
+      properties:
+        path:
+          type: string
+        pattern:
+          type: string
+      additionalProperties: false
+      required:
+        - path
 
   properties:
     schema:
@@ -92,15 +102,12 @@ data:
             type: object
             properties:
               dest:
-                type: object
-                properties:
-                  path:
-                    type: string
-                  pattern:
-                    type: string
-                additionalProperties: false
-                required:
-                  - path
+                anyOf:
+                  - $ref: "#/definitions/substitution_dest"
+                  - type: array
+                    minItems: 1
+                    items:
+                      $ref: "#/definitions/substitution_dest"
               src:
                 type: object
                 properties:
diff --git a/deckhand/tests/functional/gabbits/substitution/substitution-source-feeds-multi-dest.yaml b/deckhand/tests/functional/gabbits/substitution/substitution-source-feeds-multi-dest.yaml
new file mode 100644
index 00000000..2eddf647
--- /dev/null
+++ b/deckhand/tests/functional/gabbits/substitution/substitution-source-feeds-multi-dest.yaml
@@ -0,0 +1,82 @@
+# Tests success path for substitutions involving a single substitution source
+# feeding multiple destionation paths.
+#
+# 1. Purges existing data to ensure test isolation
+# 2. Creates necessary substitution documents.
+# 3. Validates that the destination document has the expected data across all
+#    expected destination paths.
+
+defaults:
+  request_headers:
+    content-type: application/x-yaml
+  response_headers:
+    content-type: application/x-yaml
+  verbose: true
+
+tests:
+  - name: purge
+    desc: Begin testing from known state.
+    DELETE: /api/v1.0/revisions
+    status: 204
+    response_headers: null
+
+  - name: add_substitution_source_with_single_source_multi_dest
+    desc: |-
+      Create documents to test a single substitution source document feeding
+      multiple destination paths.
+    PUT: /api/v1.0/buckets/a/documents
+    status: 200
+    data: |-
+      ---
+      schema: deckhand/LayeringPolicy/v1
+      metadata:
+        schema: metadata/Control/v1
+        name: layering-policy
+      data:
+        layerOrder:
+          - site
+      ---
+      schema: deckhand/Certificate/v1
+      metadata:
+        name: example-cert
+        schema: metadata/Document/v1
+        layeringDefinition:
+          layer: site
+        storagePolicy: cleartext
+      data: |
+        CERTIFICATE DATA
+      ---
+      schema: armada/Chart/v1
+      metadata:
+        name: example-chart-01
+        schema: metadata/Document/v1
+        layeringDefinition:
+          layer: site
+        substitutions:
+          - dest:
+              - path: .chart.values.tls.certificate
+              - path: .chart.values.tls.duplicate_certificate
+            src:
+              schema: deckhand/Certificate/v1
+              name: example-cert
+              path: .
+      data: {}
+      ...
+
+  - name: verify_substitutions
+    desc: Check for expected substitutions
+    GET: /api/v1.0/revisions/$RESPONSE['$.[0].status.revision']/rendered-documents
+    query_parameters:
+      schema: armada/Chart/v1
+    status: 200
+    response_multidoc_jsonpaths:
+      $.`len`: 1
+      $.[*].metadata.name: example-chart-01
+      $.[*].data:
+        chart:
+          values:
+            tls:
+              certificate: |
+                CERTIFICATE DATA
+              duplicate_certificate: |
+                CERTIFICATE DATA
diff --git a/tools/gate/roles/run-functional-tests/tasks/functional-tests.yaml b/tools/gate/roles/run-functional-tests/tasks/functional-tests.yaml
index f7899774..45ef6e1a 100644
--- a/tools/gate/roles/run-functional-tests/tasks/functional-tests.yaml
+++ b/tools/gate/roles/run-functional-tests/tasks/functional-tests.yaml
@@ -22,4 +22,4 @@
     DECKHAND_TEST_URL: "127.0.0.1:9000"
     DECKHAND_TEST_DIR: "{{ airship_deckhand_path.stdout }}/deckhand/tests/functional/gabbits"
   register: result
-  failed_when: "'Done SUCCESS' not in result.stdout and 'PASSED' not in result.stdout"
+  failed_when: "'commands failed' in result.stdout"
diff --git a/tools/gate/roles/run-integration-tests/tasks/integration-tests.yaml b/tools/gate/roles/run-integration-tests/tasks/integration-tests.yaml
index b055667c..03118b53 100644
--- a/tools/gate/roles/run-integration-tests/tasks/integration-tests.yaml
+++ b/tools/gate/roles/run-integration-tests/tasks/integration-tests.yaml
@@ -27,4 +27,4 @@
     DECKHAND_TEST_URL: "127.0.0.1:9000"
     DECKHAND_TEST_DIR: "{{ airship_deckhand_path.stdout }}/deckhand/tests/integration/gabbits"
   register: result
-  failed_when: "'Done SUCCESS' not in result.stdout and 'PASSED' not in result.stdout"
+  failed_when: "'commands failed' in result.stdout"