diff --git a/packages/cli/cli/versions.yml b/packages/cli/cli/versions.yml
index 7c11ca83172..f4ba3f926cd 100644
--- a/packages/cli/cli/versions.yml
+++ b/packages/cli/cli/versions.yml
@@ -1,3 +1,21 @@
+- changelogEntry: 
+    - summary: | 
+        The API V2 configuration (in beta) now supports global header overrides.
+        This fixes a bug where those header overrides were getting dropped in 
+        certain cases.
+
+        ```yml generators.yml
+        api: 
+          headers: 
+            X-API-VERSION: string
+          specs: 
+            - openapi: /path/to/openapi
+              overrides: /path/to/overrides
+        ```
+      type: fix
+  irVersion: 53
+  version: 0.42.8
+
 - changelogEntry: 
     - summary: | 
         The API V2 configuration (in beta) now supports global header 
diff --git a/packages/cli/ete-tests/src/tests/write-definition/__snapshots__/writeDefinition.test.ts.snap b/packages/cli/ete-tests/src/tests/write-definition/__snapshots__/writeDefinition.test.ts.snap
index 7294ef4ba14..f4cafbdd012 100644
--- a/packages/cli/ete-tests/src/tests/write-definition/__snapshots__/writeDefinition.test.ts.snap
+++ b/packages/cli/ete-tests/src/tests/write-definition/__snapshots__/writeDefinition.test.ts.snap
@@ -97,6 +97,105 @@ service:
 ]
 `;
 
+exports[`validate header overrides > header-overrides 1`] = `
+[
+  {
+    "contents": "types:
+  Pet:
+    properties:
+      id: long
+      name: string
+      tag: optional<string>
+    source:
+      openapi: openapi/openapi.yml
+  Pets: list<Pet>
+  Error:
+    properties:
+      code: integer
+      message: string
+    source:
+      openapi: openapi/openapi.yml
+",
+    "name": "__package__.yml",
+    "type": "file",
+  },
+  {
+    "contents": "name: api
+error-discrimination:
+  strategy: status-code
+display-name: Swagger Petstore
+environments:
+  Default: http://petstore.swagger.io/v1
+default-environment: Default
+headers:
+  X-Dummy-Header: optional<string>
+",
+    "name": "api.yml",
+    "type": "file",
+  },
+  {
+    "contents": "imports:
+  root: __package__.yml
+service:
+  auth: false
+  base-path: ''
+  endpoints:
+    listPets:
+      path: /pets
+      method: GET
+      auth: false
+      display-name: List all pets
+      request:
+        name: ListPetsRequest
+        query-parameters:
+          limit:
+            type: optional<integer>
+            docs: How many items to return at one time (max 100)
+      response:
+        docs: A paged array of pets
+        type: root.Pets
+      examples:
+        - response:
+            body:
+              - id: 1000000
+                name: name
+                tag: tag
+    createPets:
+      path: /pets
+      method: POST
+      auth: false
+      display-name: Create a pet
+      examples:
+        - {}
+    showPetById:
+      path: /pets/{petId}
+      method: GET
+      auth: false
+      path-parameters:
+        petId:
+          type: string
+          docs: The id of the pet to retrieve
+      display-name: Info for a specific pet
+      response:
+        docs: Expected response to a valid request
+        type: root.Pet
+      examples:
+        - path-parameters:
+            petId: petId
+          response:
+            body:
+              id: 1000000
+              name: name
+              tag: tag
+  source:
+    openapi: openapi/openapi.yml
+",
+    "name": "pets.yml",
+    "type": "file",
+  },
+]
+`;
+
 exports[`validate namespaced API > namespaced 1`] = `
 [
   {
diff --git a/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/__package__.yml b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/__package__.yml
new file mode 100644
index 00000000000..4f2c9816dd5
--- /dev/null
+++ b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/__package__.yml
@@ -0,0 +1,15 @@
+types:
+  Pet:
+    properties:
+      id: long
+      name: string
+      tag: optional<string>
+    source:
+      openapi: openapi/openapi.yml
+  Pets: list<Pet>
+  Error:
+    properties:
+      code: integer
+      message: string
+    source:
+      openapi: openapi/openapi.yml
diff --git a/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/api.yml b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/api.yml
new file mode 100644
index 00000000000..83ac41e9b2d
--- /dev/null
+++ b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/api.yml
@@ -0,0 +1,9 @@
+name: api
+error-discrimination:
+  strategy: status-code
+display-name: Swagger Petstore
+environments:
+  Default: http://petstore.swagger.io/v1
+default-environment: Default
+headers:
+  X-Dummy-Header: optional<string>
diff --git a/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/pets.yml b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/pets.yml
new file mode 100644
index 00000000000..ddf187ef9e0
--- /dev/null
+++ b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/.definition/pets.yml
@@ -0,0 +1,55 @@
+imports:
+  root: __package__.yml
+service:
+  auth: false
+  base-path: ''
+  endpoints:
+    listPets:
+      path: /pets
+      method: GET
+      auth: false
+      display-name: List all pets
+      request:
+        name: ListPetsRequest
+        query-parameters:
+          limit:
+            type: optional<integer>
+            docs: How many items to return at one time (max 100)
+      response:
+        docs: A paged array of pets
+        type: root.Pets
+      examples:
+        - response:
+            body:
+              - id: 1000000
+                name: name
+                tag: tag
+    createPets:
+      path: /pets
+      method: POST
+      auth: false
+      display-name: Create a pet
+      examples:
+        - {}
+    showPetById:
+      path: /pets/{petId}
+      method: GET
+      auth: false
+      path-parameters:
+        petId:
+          type: string
+          docs: The id of the pet to retrieve
+      display-name: Info for a specific pet
+      response:
+        docs: Expected response to a valid request
+        type: root.Pet
+      examples:
+        - path-parameters:
+            petId: petId
+          response:
+            body:
+              id: 1000000
+              name: name
+              tag: tag
+  source:
+    openapi: openapi/openapi.yml
diff --git a/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/fern.config.json b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/fern.config.json
new file mode 100644
index 00000000000..4168d955f58
--- /dev/null
+++ b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/fern.config.json
@@ -0,0 +1,4 @@
+{
+  "version": "*",
+  "organization": "fern"
+}
\ No newline at end of file
diff --git a/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/generators.yml b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/generators.yml
new file mode 100644
index 00000000000..eeee8eb7f3d
--- /dev/null
+++ b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/generators.yml
@@ -0,0 +1,6 @@
+api: 
+  headers: 
+    X-Dummy-Header: optional<string>
+  specs: 
+    - openapi: openapi/openapi.yml
+groups: {}
diff --git a/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/openapi/openapi.yml b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/openapi/openapi.yml
new file mode 100644
index 00000000000..f5b955a22e5
--- /dev/null
+++ b/packages/cli/ete-tests/src/tests/write-definition/fixtures/header-overrides/fern/openapi/openapi.yml
@@ -0,0 +1,113 @@
+openapi: "3.0.0"
+info:
+  version: 1.0.0
+  title: Swagger Petstore
+  license:
+    name: MIT
+servers:
+  - url: http://petstore.swagger.io/v1
+paths:
+  /pets:
+    get:
+      summary: List all pets
+      operationId: listPets
+      tags:
+        - pets
+      parameters:
+        - name: limit
+          in: query
+          description: How many items to return at one time (max 100)
+          required: false
+          schema:
+            type: integer
+            maximum: 100
+            format: int32
+      responses:
+        "200":
+          description: A paged array of pets
+          headers:
+            x-next:
+              description: A link to the next page of responses
+              schema:
+                type: string
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/Pets"
+        default:
+          description: unexpected error
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/Error"
+    post:
+      summary: Create a pet
+      operationId: createPets
+      tags:
+        - pets
+      responses:
+        "201":
+          description: Null response
+        default:
+          description: unexpected error
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/Error"
+  /pets/{petId}:
+    get:
+      summary: Info for a specific pet
+      operationId: showPetById
+      tags:
+        - pets
+      parameters:
+        - name: petId
+          in: path
+          required: true
+          description: The id of the pet to retrieve
+          schema:
+            type: string
+      responses:
+        "200":
+          description: Expected response to a valid request
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/Pet"
+        default:
+          description: unexpected error
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/Error"
+components:
+  schemas:
+    Pet:
+      type: object
+      required:
+        - id
+        - name
+      properties:
+        id:
+          type: integer
+          format: int64
+        name:
+          type: string
+        tag:
+          type: string
+    Pets:
+      type: array
+      maxItems: 100
+      items:
+        $ref: "#/components/schemas/Pet"
+    Error:
+      type: object
+      required:
+        - code
+        - message
+      properties:
+        code:
+          type: integer
+          format: int32
+        message:
+          type: string
diff --git a/packages/cli/ete-tests/src/tests/write-definition/writeDefinition.test.ts b/packages/cli/ete-tests/src/tests/write-definition/writeDefinition.test.ts
index d2ec327e24a..61218ca3cb9 100644
--- a/packages/cli/ete-tests/src/tests/write-definition/writeDefinition.test.ts
+++ b/packages/cli/ete-tests/src/tests/write-definition/writeDefinition.test.ts
@@ -22,6 +22,10 @@ describe("validate namespaced API from Cohere", () => {
     itFixture("namespaced-fleshedout");
 });
 
+describe("validate header overrides", () => {
+    itFixture("header-overrides");
+});
+
 function itFixture(fixtureName: string) {
     it(
         // eslint-disable-next-line jest/valid-title
diff --git a/packages/cli/workspace-loader/src/workspaces/OSSWorkspace.ts b/packages/cli/workspace-loader/src/workspaces/OSSWorkspace.ts
index 756db781f01..b670f5a18d5 100644
--- a/packages/cli/workspace-loader/src/workspaces/OSSWorkspace.ts
+++ b/packages/cli/workspace-loader/src/workspaces/OSSWorkspace.ts
@@ -105,7 +105,7 @@ export class OSSWorkspace extends AbstractAPIWorkspace<OSSWorkspace.Settings> {
                     : undefined,
             globalHeaderOverrides:
                 this.generatorsConfiguration?.api?.headers != null
-                    ? this.generatorsConfiguration?.api?.headers
+                    ? { ...this.generatorsConfiguration?.api }
                     : undefined,
             taskContext: context,
             ir: openApiIr,