diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingSession.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingSession.ts
index 0ab0e5851cd..7c82b966921 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingSession.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingSession.ts
@@ -836,6 +836,8 @@ export class ChatEditingSession extends Disposable implements IChatEditingSessio
 			return entry.getCurrentSnapshot();
 		} else if (entry instanceof ChatEditingModifiedDocumentEntry) {
 			return entry.getCurrentContents();
+		} else if (entry instanceof ChatEditingDeletedFileEntry) {
+			return '';
 		} else {
 			throw new Error(`unknown entry type for ${entry.modifiedURI}`);
 		}
@@ -973,10 +975,30 @@ export class ChatEditingSession extends Disposable implements IChatEditingSessio
 
 		const existingEntry = this._entriesObs.get().find(e => isEqual(e.modifiedURI, resource));
 		if (existingEntry) {
-			if (telemetryInfo.requestId !== existingEntry.telemetryInfo.requestId) {
-				existingEntry.updateTelemetryInfo(telemetryInfo);
+			// If the existing entry is a deleted file entry, we need to replace it with a new modified entry
+			// This handles the case where a file was deleted and then recreated
+			if (existingEntry instanceof ChatEditingDeletedFileEntry) {
+				// Use the original content from the deleted entry as the initial content for the new entry
+				const initialContentFromDeleted = existingEntry.state.get() === ModifiedFileEntryState.Modified
+					? existingEntry.initialContent
+					: undefined;
+
+				// Remove the deleted entry
+				existingEntry.dispose();
+				const entries = this._entriesObs.get().filter(e => e !== existingEntry);
+				this._entriesObs.set(entries, undefined);
+
+				// Set the initial content from the deleted entry if it was still in modified state
+				if (initialContentFromDeleted !== undefined) {
+					_initialContent = initialContentFromDeleted;
+				}
+				// Fall through to create a new entry
+			} else {
+				if (telemetryInfo.requestId !== existingEntry.telemetryInfo.requestId) {
+					existingEntry.updateTelemetryInfo(telemetryInfo);
+				}
+				return existingEntry;
 			}
-			return existingEntry;
 		}
 
 		let entry: AbstractChatEditingModifiedFileEntry;