diff --git a/tests/e2e/cucumber/features/app-provider/officeSuites.feature b/tests/e2e/cucumber/features/app-provider/officeSuites.feature
index 207485ce1f..d74ba3faaf 100644
--- a/tests/e2e/cucumber/features/app-provider/officeSuites.feature
+++ b/tests/e2e/cucumber/features/app-provider/officeSuites.feature
@@ -144,3 +144,13 @@ Feature: Integration with Collabora online office
       | resource          |
       | Template (1).docx |
     And "Alice" logs out
+
+
+  Scenario: open the file using the context menu
+    When "Alice" logs in
+    And "Alice" opens file "new.txt" via "collabora" using the context menu
+    Then "Alice" should see the content "test content" in editor "Collabora"
+    And "Alice" closes the file viewer
+    When "Alice" opens file "new.txt" via "text-editor" using the context menu
+    And "Alice" closes the file viewer
+    And "Alice" logs out
diff --git a/tests/e2e/cucumber/steps/ui/resources.ts b/tests/e2e/cucumber/steps/ui/resources.ts
index c4e2b3c98b..f235ac403e 100644
--- a/tests/e2e/cucumber/steps/ui/resources.ts
+++ b/tests/e2e/cucumber/steps/ui/resources.ts
@@ -1098,3 +1098,18 @@ Then(
     await expect(avatarLocator).toBeVisible()
   }
 )
+
+When(
+  '{string} opens file {string} via {string} using the context menu',
+  async function (this: World, stepUser: string, file: string, fileViewer: string): Promise<void> {
+    const allowedViewers = ['collabora', 'text-editor', 'preview'] as const
+
+    if (!allowedViewers.includes(fileViewer as any)) {
+      throw new Error(`Unsupported file viewer: ${fileViewer}`)
+    }
+    const { page } = this.actorsEnvironment.getActor({ key: stepUser })
+    const resourceObject = new objects.applicationFiles.Resource({ page })
+
+    await resourceObject.openFileViaContextMenu(file, fileViewer as (typeof allowedViewers)[number])
+  }
+)
diff --git a/tests/e2e/support/objects/app-files/resource/actions.ts b/tests/e2e/support/objects/app-files/resource/actions.ts
index 71cd4811a1..eda6865be6 100644
--- a/tests/e2e/support/objects/app-files/resource/actions.ts
+++ b/tests/e2e/support/objects/app-files/resource/actions.ts
@@ -146,6 +146,7 @@ const fileIconPreview = '#oc-file-details-sidebar .details-preview'
 const activitySidebarPanel = 'sidebar-panel-activities'
 const activitySidebarPanelBodyContent = '#sidebar-panel-activities .sidebar-panel__body-content'
 const contextMenuAction = '//*[@id="oc-files-context-actions-context"]//span[text()="%s"]'
+const openWithAction = '.oc-files-actions-%s-trigger'
 
 export const clickResource = async ({
   page,
@@ -2268,3 +2269,21 @@ export const getAvatarLocatorFromActivityPanel = async (args: {
     .locator(util.format(userAvatarInActivitypanelSelector, user.username))
     .locator('img')
 }
+
+export const openFileViaContextMenu = async ({
+  page,
+  resource,
+  fileViewer
+}: {
+  page: Page
+  resource: string
+  fileViewer: string
+}): Promise<void> => {
+  await page.locator(util.format(resourceNameSelector, resource)).click({ button: 'right' })
+  const openWith = page.locator(util.format(contextMenuAction, 'Open with...'))
+  await openWith.hover()
+
+  const editorItem = page.locator(util.format(openWithAction, fileViewer))
+  await expect(editorItem).toBeVisible()
+  await editorItem.click()
+}
diff --git a/tests/e2e/support/objects/app-files/resource/index.ts b/tests/e2e/support/objects/app-files/resource/index.ts
index 275b9cba33..04c0db790e 100644
--- a/tests/e2e/support/objects/app-files/resource/index.ts
+++ b/tests/e2e/support/objects/app-files/resource/index.ts
@@ -413,4 +413,8 @@ export class Resource {
   }): Promise<Locator> {
     return await po.getAvatarLocatorFromActivityPanel({ page: this.#page, ...args })
   }
+
+  async openFileViaContextMenu(resource: string, fileViewer: string): Promise<void> {
+    await po.openFileViaContextMenu({ page: this.#page, resource, fileViewer })
+  }
 }