diff --git a/src/routes/chat.ts b/src/routes/chat.ts
index 6856500..90568ff 100644
--- a/src/routes/chat.ts
+++ b/src/routes/chat.ts
@@ -129,6 +129,26 @@ const createInitialStreamingMessages = (existingMessages: unknown[], userContent
   ];
 };
 
+const countFrontendUserMessages = (messages: unknown[]) =>
+  messages.filter(
+    (message) => isObjectRecord(message) && message.role === "user",
+  ).length;
+
+const pruneBranchGroupsForMessageIndex = (
+  branchGroups: unknown[],
+  messageIndex: number | undefined,
+) => {
+  if (messageIndex === undefined) {
+    return branchGroups;
+  }
+  return branchGroups.filter(
+    (group) =>
+      !isObjectRecord(group) ||
+      typeof group.parentCount !== "number" ||
+      group.parentCount < messageIndex,
+  );
+};
+
 const upsertBackendProgress = (
   progress: unknown,
   payload: Record<string, unknown>,
@@ -952,15 +972,24 @@ export const buildChatRouter = (
         projectKey: requestContext.projectKey,
         sessionId: requestContext.clientSessionId,
       };
-      const recentTurns = await sessionTranscriptStore.getRecentTurns(historyContext, 8);
       const initialSessionState = await sessionUiStateStore.read(
         toSessionUiStateContext(activeSessionRecord),
       );
       const persistedMessages = initialSessionState?.messages ?? [];
+      const isRegenerate =
+        parsed.data.regenerate_from_message_index !== undefined;
       const baseMessages =
-        parsed.data.regenerate_from_message_index !== undefined
+        isRegenerate
           ? persistedMessages.slice(0, parsed.data.regenerate_from_message_index)
           : persistedMessages;
+      const targetUserOrdinal = isRegenerate
+        ? countFrontendUserMessages(
+            persistedMessages.slice(
+              0,
+              (parsed.data.regenerate_from_message_index ?? 0) + 1,
+            ),
+          )
+        : undefined;
       if (activeRuns.get(activeSessionRecord.sessionId)?.status === "running") {
         res.status(409).json({
           message: "session is already streaming",
@@ -968,6 +997,15 @@ export const buildChatRouter = (
         });
         return;
       }
+      if (isRegenerate) {
+        await sessionTranscriptStore.truncateThread(
+          historyContext,
+          parsed.data.regenerate_from_message_index ?? 0,
+        );
+      }
+      const recentTurns = isRegenerate
+        ? []
+        : await sessionTranscriptStore.getRecentTurns(historyContext, 8);
 
       logger.info(
         {
@@ -976,6 +1014,7 @@ export const buildChatRouter = (
           created: created || sessionCreated,
           model: parsed.data.model,
           approvalMode: parsed.data.approval_mode,
+          regenerateFromMessageIndex: parsed.data.regenerate_from_message_index,
           traceId: requestContext.traceId,
           projectId: requestContext.projectId,
         },
@@ -997,7 +1036,10 @@ export const buildChatRouter = (
         baseMessages,
         parsed.data.message,
       );
-      const branchGroups = initialSessionState?.branchGroups ?? [];
+      const branchGroups = pruneBranchGroupsForMessageIndex(
+        initialSessionState?.branchGroups ?? [],
+        parsed.data.regenerate_from_message_index,
+      );
       const activeRun: ActiveRun = {
         clientSessionId,
         controller: abortController,
@@ -1128,8 +1170,13 @@ export const buildChatRouter = (
       };
 
       try {
-        if (parsed.data.regenerate_from_message_index !== undefined) {
-          await runtime.revertLastUserMessage(binding.sessionId);
+        if (isRegenerate) {
+          if (!targetUserOrdinal || targetUserOrdinal < 1) {
+            throw new Error("target user message not found for regeneration");
+          }
+          await runtime.revertToUserMessage(binding.sessionId, {
+            userOrdinal: targetUserOrdinal,
+          });
         }
 
         const preparedMessage = await buildPromptWithLearningContext(
diff --git a/src/runtime/opencode.ts b/src/runtime/opencode.ts
index 7da7e3a..15ae31c 100644
--- a/src/runtime/opencode.ts
+++ b/src/runtime/opencode.ts
@@ -33,6 +33,16 @@ type RuntimeModelOverride = {
 
 export type PermissionReply = "once" | "always" | "reject";
 
+type RuntimeMessage = {
+  info: {
+    id: string;
+    role: string;
+  };
+};
+
+const getRuntimeMessageRole = (message: RuntimeMessage) => message.info.role;
+const getRuntimeMessageId = (message: RuntimeMessage) => message.info.id;
+
 export class OpencodeRuntimeAdapter {
   private clientPromise: Promise<OpencodeClient> | null = null;
   private closeServer: (() => void) | null = null;
@@ -108,17 +118,45 @@ export class OpencodeRuntimeAdapter {
     return response.data;
   }
 
-  async revertLastUserMessage(sessionId: string) {
-    const messages = await this.messages(sessionId, 40);
-    const lastUserMessage = [...messages]
-      .reverse()
-      .find((message) => message.info.role === "user");
+  async removeMessage(sessionId: string, messageId: string) {
+    const client = await this.ensureClient();
+    const response = await client.session.deleteMessage({
+      sessionID: sessionId,
+      messageID: messageId,
+    });
+    return response.data;
+  }
 
-    if (!lastUserMessage) {
-      throw new Error("no user message found to revert");
+  async revertToUserMessage(sessionId: string, options: { userOrdinal: number }) {
+    const messages = await this.messages(sessionId, 80);
+    const userMessages = messages.filter(
+      (message) => getRuntimeMessageRole(message) === "user",
+    );
+    const targetUserMessage = userMessages[options.userOrdinal - 1];
+
+    if (!targetUserMessage) {
+      throw new Error("target user message not found to revert");
     }
 
-    return this.revertMessage(sessionId, lastUserMessage.info.id);
+    const targetMessageId = getRuntimeMessageId(targetUserMessage);
+    const targetIndex = messages.findIndex(
+      (message) => getRuntimeMessageId(message) === targetMessageId,
+    );
+    const messagesToRemove = targetIndex >= 0 ? messages.slice(targetIndex) : [targetUserMessage];
+
+    await this.revertMessage(sessionId, targetMessageId);
+
+    for (const message of messagesToRemove.reverse()) {
+      const messageId = getRuntimeMessageId(message);
+      try {
+        await this.removeMessage(sessionId, messageId);
+      } catch (error) {
+        logger.warn(
+          { err: error, sessionId, messageId },
+          "failed to remove reverted opencode message",
+        );
+      }
+    }
   }
 
   async abortSession(sessionId: string) {
diff --git a/src/sessions/transcriptStore.ts b/src/sessions/transcriptStore.ts
index bbe3f14..09e2237 100644
--- a/src/sessions/transcriptStore.ts
+++ b/src/sessions/transcriptStore.ts
@@ -147,6 +147,29 @@ export class SessionTranscriptStore {
     return nextTranscript;
   }
 
+  async truncateThread(
+    context: SessionTranscriptContext,
+    keepMessageCount: number,
+  ) {
+    const key = this.filePath(context);
+    return this.serializeWrite(key, async () => {
+      const transcript = await this.readTranscript(context);
+      if (!transcript) {
+        return null;
+      }
+
+      const nextTranscript: SessionTranscriptRecord = {
+        ...transcript,
+        clientSessionId: context.clientSessionId ?? transcript.clientSessionId,
+        sessionId: context.sessionId,
+        turns: projectTurnsForFork(transcript.turns, keepMessageCount),
+        updatedAt: new Date().toISOString(),
+      };
+      await atomicWriteJson(key, nextTranscript);
+      return nextTranscript;
+    });
+  }
+
   async search(
     context: Pick<SessionTranscriptContext, "actorKey" | "projectKey">,
     query: string,