diff --git a/cypress/e2e/files_sharing/files-copy-move.cy.ts b/cypress/e2e/files_sharing/files-copy-move.cy.ts
index 16d07c3d40c20..7c0272248d309 100644
--- a/cypress/e2e/files_sharing/files-copy-move.cy.ts
+++ b/cypress/e2e/files_sharing/files-copy-move.cy.ts
@@ -19,44 +19,52 @@ export function copyFileForbidden(fileName: string, dirPath: string) {
 	getRowForFile(fileName).should('be.visible')
 	triggerActionForFile(fileName, ACTION_COPY_MOVE)
 
-	cy.get('.file-picker').within(() => {
-		// intercept the copy so we can wait for it
-		cy.intercept('COPY', /\/(remote|public)\.php\/dav\/files\//).as('copyFile')
-
-		const directories = dirPath.split('/')
-		directories.forEach((directory) => {
-			// select the folder
-			cy.get(`[data-filename="${CSS.escape(directory)}"]`).should('be.visible').click()
-		})
+	cy.get('.file-picker').should('be.visible')
 
-		// check copy button
-		cy.contains('button', `Copy to ${directories.at(-1)}`).should('be.disabled')
+	const directories = dirPath.split('/')
+	directories.forEach((directory) => {
+		cy.get('.file-picker')
+			.find(`[data-filename="${CSS.escape(directory)}"]`)
+			.should('be.visible')
+			.click()
 	})
+
+	// Re-query after possible re-render and assert eventual disabled state
+	cy.get('.file-picker')
+		.contains('button', `Copy to ${directories.at(-1)}`, { timeout: 10000 })
+		.should('be.visible')
+		.and('be.disabled')
 }
 
 export function moveFileForbidden(fileName: string, dirPath: string) {
 	getRowForFile(fileName).should('be.visible')
 	triggerActionForFile(fileName, ACTION_COPY_MOVE)
 
-	cy.get('.file-picker').within(() => {
-		// intercept the copy so we can wait for it
-		cy.intercept('MOVE', /\/(remote|public)\.php\/dav\/files\//).as('moveFile')
+	cy.get('.file-picker').should('be.visible')
 
-		// select home folder
-		cy.get('.breadcrumb')
-			.findByRole('button', { name: 'All files' })
-			.should('be.visible')
-			.click()
+	// Avoid stale chained subject when breadcrumb re-renders
+	cy.get('.file-picker .breadcrumb')
+		.findByRole('button', { name: 'All files' })
+		.should('be.visible')
+		.click()
 
-		const directories = dirPath.split('/')
-		directories.forEach((directory) => {
-			// select the folder
-			cy.get(`[data-filename="${directory}"]`).should('be.visible').click()
-		})
+	// Re-acquire file picker after navigation click
+	cy.get('.file-picker').should('be.visible')
 
-		// click move
-		cy.contains('button', `Move to ${directories.at(-1)}`).should('not.exist')
+	const directories = dirPath.split('/')
+	directories.forEach((directory) => {
+		cy.get('.file-picker')
+			.find(`[data-filename="${CSS.escape(directory)}"]`)
+			.should('be.visible')
+			.click()
 	})
+
+	// If move is forbidden, the move button should not be present.
+	// Use should('not.contain') on the parent to avoid the cy.contains() + should('not.exist')
+	// anti-pattern, where cy.contains() must first find the element before the negation can pass,
+	// causing unnecessary waits or false failures.
+	cy.get('.file-picker', { timeout: 10000 })
+		.should('not.contain', `Move to ${directories.at(-1)}`)
 }
 
 describe('files_sharing: Move or copy files', { testIsolation: true }, () => {