Import worktree documents and attachments

Co-Authored-By: Paperclip <noreply@paperclip.ing>
2026-03-20 15:59:41 -05:00
parent be911754c5
commit 73ada45037
3 changed files with 1083 additions and 20 deletions
--- a/cli/src/tests/worktree-merge-history.test.ts
+++ b/cli/src/tests/worktree-merge-history.test.ts
@@ -53,6 +53,68 @@ function makeComment(overrides: Record<string, unknown> = {}) {
  } as any;
 }

+function makeIssueDocument(overrides: Record<string, unknown> = {}) {
+  return {
+    id: "issue-document-1",
+    companyId: "company-1",
+    issueId: "issue-1",
+    documentId: "document-1",
+    key: "plan",
+    linkCreatedAt: new Date("2026-03-20T00:00:00.000Z"),
+    linkUpdatedAt: new Date("2026-03-20T00:00:00.000Z"),
+    title: "Plan",
+    format: "markdown",
+    latestBody: "# Plan",
+    latestRevisionId: "revision-1",
+    latestRevisionNumber: 1,
+    createdByAgentId: null,
+    createdByUserId: "local-board",
+    updatedByAgentId: null,
+    updatedByUserId: "local-board",
+    documentCreatedAt: new Date("2026-03-20T00:00:00.000Z"),
+    documentUpdatedAt: new Date("2026-03-20T00:00:00.000Z"),
+    ...overrides,
+  } as any;
+}
+
+function makeDocumentRevision(overrides: Record<string, unknown> = {}) {
+  return {
+    id: "revision-1",
+    companyId: "company-1",
+    documentId: "document-1",
+    revisionNumber: 1,
+    body: "# Plan",
+    changeSummary: null,
+    createdByAgentId: null,
+    createdByUserId: "local-board",
+    createdAt: new Date("2026-03-20T00:00:00.000Z"),
+    ...overrides,
+  } as any;
+}
+
+function makeAttachment(overrides: Record<string, unknown> = {}) {
+  return {
+    id: "attachment-1",
+    companyId: "company-1",
+    issueId: "issue-1",
+    issueCommentId: null,
+    assetId: "asset-1",
+    provider: "local_disk",
+    objectKey: "company-1/issues/issue-1/2026/03/20/asset.png",
+    contentType: "image/png",
+    byteSize: 12,
+    sha256: "deadbeef",
+    originalFilename: "asset.png",
+    createdByAgentId: null,
+    createdByUserId: "local-board",
+    assetCreatedAt: new Date("2026-03-20T00:00:00.000Z"),
+    assetUpdatedAt: new Date("2026-03-20T00:00:00.000Z"),
+    attachmentCreatedAt: new Date("2026-03-20T00:00:00.000Z"),
+    attachmentUpdatedAt: new Date("2026-03-20T00:00:00.000Z"),
+    ...overrides,
+  } as any;
+}
+
 describe("worktree merge history planner", () => {
  it("parses default scopes", () => {
    expect(parseWorktreeMergeScopes(undefined)).toEqual(["issues", "comments"]);
@@ -214,4 +276,117 @@ describe("worktree merge history planner", () => {
    ]);
    expect(plan.adjustments.clear_author_agent).toBe(1);
  });
+
+  it("merges document revisions onto an existing shared document and renumbers conflicts", () => {
+    const sharedIssue = makeIssue({ id: "issue-a", identifier: "PAP-10" });
+    const sourceDocument = makeIssueDocument({
+      issueId: "issue-a",
+      documentId: "document-a",
+      latestBody: "# Branch plan",
+      latestRevisionId: "revision-branch-2",
+      latestRevisionNumber: 2,
+      documentUpdatedAt: new Date("2026-03-20T02:00:00.000Z"),
+      linkUpdatedAt: new Date("2026-03-20T02:00:00.000Z"),
+    });
+    const targetDocument = makeIssueDocument({
+      issueId: "issue-a",
+      documentId: "document-a",
+      latestBody: "# Main plan",
+      latestRevisionId: "revision-main-2",
+      latestRevisionNumber: 2,
+      documentUpdatedAt: new Date("2026-03-20T01:00:00.000Z"),
+      linkUpdatedAt: new Date("2026-03-20T01:00:00.000Z"),
+    });
+    const sourceRevisionOne = makeDocumentRevision({ documentId: "document-a", id: "revision-1" });
+    const sourceRevisionTwo = makeDocumentRevision({
+      documentId: "document-a",
+      id: "revision-branch-2",
+      revisionNumber: 2,
+      body: "# Branch plan",
+      createdAt: new Date("2026-03-20T02:00:00.000Z"),
+    });
+    const targetRevisionOne = makeDocumentRevision({ documentId: "document-a", id: "revision-1" });
+    const targetRevisionTwo = makeDocumentRevision({
+      documentId: "document-a",
+      id: "revision-main-2",
+      revisionNumber: 2,
+      body: "# Main plan",
+      createdAt: new Date("2026-03-20T01:00:00.000Z"),
+    });
+
+    const plan = buildWorktreeMergePlan({
+      companyId: "company-1",
+      companyName: "Paperclip",
+      issuePrefix: "PAP",
+      previewIssueCounterStart: 10,
+      scopes: ["issues", "comments"],
+      sourceIssues: [sharedIssue],
+      targetIssues: [sharedIssue],
+      sourceComments: [],
+      targetComments: [],
+      sourceDocuments: [sourceDocument],
+      targetDocuments: [targetDocument],
+      sourceDocumentRevisions: [sourceRevisionOne, sourceRevisionTwo],
+      targetDocumentRevisions: [targetRevisionOne, targetRevisionTwo],
+      sourceAttachments: [],
+      targetAttachments: [],
+      targetAgents: [],
+      targetProjects: [],
+      targetProjectWorkspaces: [],
+      targetGoals: [{ id: "goal-1" }] as any,
+    });
+
+    expect(plan.counts.documentsToMerge).toBe(1);
+    expect(plan.counts.documentRevisionsToInsert).toBe(1);
+    expect(plan.documentPlans[0]).toMatchObject({
+      action: "merge_existing",
+      latestRevisionId: "revision-branch-2",
+      latestRevisionNumber: 3,
+    });
+    const mergePlan = plan.documentPlans[0] as any;
+    expect(mergePlan.revisionsToInsert).toHaveLength(1);
+    expect(mergePlan.revisionsToInsert[0]).toMatchObject({
+      source: { id: "revision-branch-2" },
+      targetRevisionNumber: 3,
+    });
+  });
+
+  it("imports attachments while clearing missing comment and author references", () => {
+    const sharedIssue = makeIssue({ id: "issue-a", identifier: "PAP-10" });
+    const attachment = makeAttachment({
+      issueId: "issue-a",
+      issueCommentId: "comment-missing",
+      createdByAgentId: "agent-missing",
+    });
+
+    const plan = buildWorktreeMergePlan({
+      companyId: "company-1",
+      companyName: "Paperclip",
+      issuePrefix: "PAP",
+      previewIssueCounterStart: 10,
+      scopes: ["issues"],
+      sourceIssues: [sharedIssue],
+      targetIssues: [sharedIssue],
+      sourceComments: [],
+      targetComments: [],
+      sourceDocuments: [],
+      targetDocuments: [],
+      sourceDocumentRevisions: [],
+      targetDocumentRevisions: [],
+      sourceAttachments: [attachment],
+      targetAttachments: [],
+      targetAgents: [],
+      targetProjects: [],
+      targetProjectWorkspaces: [],
+      targetGoals: [{ id: "goal-1" }] as any,
+    });
+
+    expect(plan.counts.attachmentsToInsert).toBe(1);
+    expect(plan.adjustments.clear_attachment_agent).toBe(1);
+    expect(plan.attachmentPlans[0]).toMatchObject({
+      action: "insert",
+      targetIssueCommentId: null,
+      targetCreatedByAgentId: null,
+    });
+  });
 });
--- a/cli/src/commands/worktree-merge-history-lib.ts
+++ b/cli/src/commands/worktree-merge-history-lib.ts
@@ -1,7 +1,11 @@
 import {
  agents,
+  assets,
+  documentRevisions,
  goals,
+  issueAttachments,
  issueComments,
+  issueDocuments,
  issues,
  projects,
  projectWorkspaces,
@@ -13,6 +17,10 @@ type AgentRow = typeof agents.$inferSelect;
 type ProjectRow = typeof projects.$inferSelect;
 type ProjectWorkspaceRow = typeof projectWorkspaces.$inferSelect;
 type GoalRow = typeof goals.$inferSelect;
+type IssueDocumentLinkRow = typeof issueDocuments.$inferSelect;
+type DocumentRevisionTableRow = typeof documentRevisions.$inferSelect;
+type IssueAttachmentTableRow = typeof issueAttachments.$inferSelect;
+type AssetRow = typeof assets.$inferSelect;

 export const WORKTREE_MERGE_SCOPES = ["issues", "comments"] as const;
 export type WorktreeMergeScope = (typeof WORKTREE_MERGE_SCOPES)[number];
@@ -23,7 +31,10 @@ export type ImportAdjustment =
  | "clear_project_workspace"
  | "clear_goal"
  | "clear_author_agent"
-  | "coerce_in_progress_to_todo";
+  | "coerce_in_progress_to_todo"
+  | "clear_document_agent"
+  | "clear_document_revision_agent"
+  | "clear_attachment_agent";

 export type IssueMergeAction = "skip_existing" | "insert";
 export type CommentMergeAction = "skip_existing" | "skip_missing_parent" | "insert";
@@ -62,6 +73,106 @@ export type PlannedCommentSkip = {
  action: "skip_existing" | "skip_missing_parent";
 };

+export type IssueDocumentRow = {
+  id: IssueDocumentLinkRow["id"];
+  companyId: IssueDocumentLinkRow["companyId"];
+  issueId: IssueDocumentLinkRow["issueId"];
+  documentId: IssueDocumentLinkRow["documentId"];
+  key: IssueDocumentLinkRow["key"];
+  linkCreatedAt: IssueDocumentLinkRow["createdAt"];
+  linkUpdatedAt: IssueDocumentLinkRow["updatedAt"];
+  title: string | null;
+  format: string;
+  latestBody: string;
+  latestRevisionId: string | null;
+  latestRevisionNumber: number;
+  createdByAgentId: string | null;
+  createdByUserId: string | null;
+  updatedByAgentId: string | null;
+  updatedByUserId: string | null;
+  documentCreatedAt: Date;
+  documentUpdatedAt: Date;
+};
+
+export type DocumentRevisionRow = {
+  id: DocumentRevisionTableRow["id"];
+  companyId: DocumentRevisionTableRow["companyId"];
+  documentId: DocumentRevisionTableRow["documentId"];
+  revisionNumber: DocumentRevisionTableRow["revisionNumber"];
+  body: DocumentRevisionTableRow["body"];
+  changeSummary: DocumentRevisionTableRow["changeSummary"];
+  createdByAgentId: string | null;
+  createdByUserId: string | null;
+  createdAt: Date;
+};
+
+export type IssueAttachmentRow = {
+  id: IssueAttachmentTableRow["id"];
+  companyId: IssueAttachmentTableRow["companyId"];
+  issueId: IssueAttachmentTableRow["issueId"];
+  issueCommentId: IssueAttachmentTableRow["issueCommentId"];
+  assetId: IssueAttachmentTableRow["assetId"];
+  provider: AssetRow["provider"];
+  objectKey: AssetRow["objectKey"];
+  contentType: AssetRow["contentType"];
+  byteSize: AssetRow["byteSize"];
+  sha256: AssetRow["sha256"];
+  originalFilename: AssetRow["originalFilename"];
+  createdByAgentId: string | null;
+  createdByUserId: string | null;
+  assetCreatedAt: Date;
+  assetUpdatedAt: Date;
+  attachmentCreatedAt: Date;
+  attachmentUpdatedAt: Date;
+};
+
+export type PlannedDocumentRevisionInsert = {
+  source: DocumentRevisionRow;
+  targetRevisionNumber: number;
+  targetCreatedByAgentId: string | null;
+  adjustments: ImportAdjustment[];
+};
+
+export type PlannedIssueDocumentInsert = {
+  source: IssueDocumentRow;
+  action: "insert";
+  targetCreatedByAgentId: string | null;
+  targetUpdatedByAgentId: string | null;
+  latestRevisionId: string | null;
+  latestRevisionNumber: number;
+  revisionsToInsert: PlannedDocumentRevisionInsert[];
+  adjustments: ImportAdjustment[];
+};
+
+export type PlannedIssueDocumentMerge = {
+  source: IssueDocumentRow;
+  action: "merge_existing";
+  targetCreatedByAgentId: string | null;
+  targetUpdatedByAgentId: string | null;
+  latestRevisionId: string | null;
+  latestRevisionNumber: number;
+  revisionsToInsert: PlannedDocumentRevisionInsert[];
+  adjustments: ImportAdjustment[];
+};
+
+export type PlannedIssueDocumentSkip = {
+  source: IssueDocumentRow;
+  action: "skip_existing" | "skip_missing_parent" | "skip_conflicting_key";
+};
+
+export type PlannedAttachmentInsert = {
+  source: IssueAttachmentRow;
+  action: "insert";
+  targetIssueCommentId: string | null;
+  targetCreatedByAgentId: string | null;
+  adjustments: ImportAdjustment[];
+};
+
+export type PlannedAttachmentSkip = {
+  source: IssueAttachmentRow;
+  action: "skip_existing" | "skip_missing_parent";
+};
+
 export type WorktreeMergePlan = {
  companyId: string;
  companyName: string;
@@ -70,6 +181,8 @@ export type WorktreeMergePlan = {
  scopes: WorktreeMergeScope[];
  issuePlans: Array<PlannedIssueInsert | PlannedIssueSkip>;
  commentPlans: Array<PlannedCommentInsert | PlannedCommentSkip>;
+  documentPlans: Array<PlannedIssueDocumentInsert | PlannedIssueDocumentMerge | PlannedIssueDocumentSkip>;
+  attachmentPlans: Array<PlannedAttachmentInsert | PlannedAttachmentSkip>;
  counts: {
    issuesToInsert: number;
    issuesExisting: number;
@@ -77,6 +190,15 @@ export type WorktreeMergePlan = {
    commentsToInsert: number;
    commentsExisting: number;
    commentsMissingParent: number;
+    documentsToInsert: number;
+    documentsToMerge: number;
+    documentsExisting: number;
+    documentsConflictingKey: number;
+    documentsMissingParent: number;
+    documentRevisionsToInsert: number;
+    attachmentsToInsert: number;
+    attachmentsExisting: number;
+    attachmentsMissingParent: number;
  };
  adjustments: Record<ImportAdjustment, number>;
 };
@@ -103,6 +225,52 @@ function incrementAdjustment(
  counts[adjustment] += 1;
 }

+function groupBy<T>(rows: T[], keyFor: (row: T) => string): Map<string, T[]> {
+  const out = new Map<string, T[]>();
+  for (const row of rows) {
+    const key = keyFor(row);
+    const existing = out.get(key);
+    if (existing) {
+      existing.push(row);
+    } else {
+      out.set(key, [row]);
+    }
+  }
+  return out;
+}
+
+function sameDate(left: Date, right: Date): boolean {
+  return left.getTime() === right.getTime();
+}
+
+function sortDocumentRows(rows: IssueDocumentRow[]): IssueDocumentRow[] {
+  return [...rows].sort((left, right) => {
+    const createdDelta = left.documentCreatedAt.getTime() - right.documentCreatedAt.getTime();
+    if (createdDelta !== 0) return createdDelta;
+    const linkDelta = left.linkCreatedAt.getTime() - right.linkCreatedAt.getTime();
+    if (linkDelta !== 0) return linkDelta;
+    return left.documentId.localeCompare(right.documentId);
+  });
+}
+
+function sortDocumentRevisions(rows: DocumentRevisionRow[]): DocumentRevisionRow[] {
+  return [...rows].sort((left, right) => {
+    const revisionDelta = left.revisionNumber - right.revisionNumber;
+    if (revisionDelta !== 0) return revisionDelta;
+    const createdDelta = left.createdAt.getTime() - right.createdAt.getTime();
+    if (createdDelta !== 0) return createdDelta;
+    return left.id.localeCompare(right.id);
+  });
+}
+
+function sortAttachments(rows: IssueAttachmentRow[]): IssueAttachmentRow[] {
+  return [...rows].sort((left, right) => {
+    const createdDelta = left.attachmentCreatedAt.getTime() - right.attachmentCreatedAt.getTime();
+    if (createdDelta !== 0) return createdDelta;
+    return left.id.localeCompare(right.id);
+  });
+}
+
 function sortIssuesForImport(sourceIssues: IssueRow[]): IssueRow[] {
  const byId = new Map(sourceIssues.map((issue) => [issue.id, issue]));
  const memoDepth = new Map<string, number>();
@@ -170,6 +338,12 @@ export function buildWorktreeMergePlan(input: {
  targetIssues: IssueRow[];
  sourceComments: CommentRow[];
  targetComments: CommentRow[];
+  sourceDocuments?: IssueDocumentRow[];
+  targetDocuments?: IssueDocumentRow[];
+  sourceDocumentRevisions?: DocumentRevisionRow[];
+  targetDocumentRevisions?: DocumentRevisionRow[];
+  sourceAttachments?: IssueAttachmentRow[];
+  targetAttachments?: IssueAttachmentRow[];
  targetAgents: AgentRow[];
  targetProjects: ProjectRow[];
  targetProjectWorkspaces: ProjectWorkspaceRow[];
@@ -192,6 +366,9 @@ export function buildWorktreeMergePlan(input: {
    clear_goal: 0,
    clear_author_agent: 0,
    coerce_in_progress_to_todo: 0,
+    clear_document_agent: 0,
+    clear_document_revision_agent: 0,
+    clear_attachment_agent: 0,
  };

  const issuePlans: Array<PlannedIssueInsert | PlannedIssueSkip> = [];
@@ -324,6 +501,176 @@ export function buildWorktreeMergePlan(input: {
    }
  }

+  const sourceDocuments = input.sourceDocuments ?? [];
+  const targetDocuments = input.targetDocuments ?? [];
+  const sourceDocumentRevisions = input.sourceDocumentRevisions ?? [];
+  const targetDocumentRevisions = input.targetDocumentRevisions ?? [];
+
+  const targetDocumentsById = new Map(targetDocuments.map((document) => [document.documentId, document]));
+  const targetDocumentsByIssueKey = new Map(targetDocuments.map((document) => [`${document.issueId}:${document.key}`, document]));
+  const sourceRevisionsByDocumentId = groupBy(sourceDocumentRevisions, (revision) => revision.documentId);
+  const targetRevisionsByDocumentId = groupBy(targetDocumentRevisions, (revision) => revision.documentId);
+  const commentIdsAvailableAfterImport = new Set<string>([
+    ...input.targetComments.map((comment) => comment.id),
+    ...commentPlans.filter((plan): plan is PlannedCommentInsert => plan.action === "insert").map((plan) => plan.source.id),
+  ]);
+
+  const documentPlans: Array<PlannedIssueDocumentInsert | PlannedIssueDocumentMerge | PlannedIssueDocumentSkip> = [];
+  for (const document of sortDocumentRows(sourceDocuments)) {
+    if (!issueIdsAvailableAfterImport.has(document.issueId)) {
+      documentPlans.push({ source: document, action: "skip_missing_parent" });
+      continue;
+    }
+
+    const existingDocument = targetDocumentsById.get(document.documentId);
+    const conflictingIssueKeyDocument = targetDocumentsByIssueKey.get(`${document.issueId}:${document.key}`);
+    if (!existingDocument && conflictingIssueKeyDocument && conflictingIssueKeyDocument.documentId !== document.documentId) {
+      documentPlans.push({ source: document, action: "skip_conflicting_key" });
+      continue;
+    }
+
+    const adjustments: ImportAdjustment[] = [];
+    const targetCreatedByAgentId =
+      document.createdByAgentId && targetAgentIds.has(document.createdByAgentId) ? document.createdByAgentId : null;
+    const targetUpdatedByAgentId =
+      document.updatedByAgentId && targetAgentIds.has(document.updatedByAgentId) ? document.updatedByAgentId : null;
+    if (
+      (document.createdByAgentId && !targetCreatedByAgentId)
+      || (document.updatedByAgentId && !targetUpdatedByAgentId)
+    ) {
+      adjustments.push("clear_document_agent");
+      incrementAdjustment(adjustmentCounts, "clear_document_agent");
+    }
+
+    const sourceRevisions = sortDocumentRevisions(sourceRevisionsByDocumentId.get(document.documentId) ?? []);
+    const targetRevisions = sortDocumentRevisions(targetRevisionsByDocumentId.get(document.documentId) ?? []);
+    const existingRevisionIds = new Set(targetRevisions.map((revision) => revision.id));
+    const usedRevisionNumbers = new Set(targetRevisions.map((revision) => revision.revisionNumber));
+    let nextRevisionNumber = targetRevisions.reduce(
+      (maxValue, revision) => Math.max(maxValue, revision.revisionNumber),
+      0,
+    ) + 1;
+
+    const targetRevisionNumberById = new Map<string, number>(
+      targetRevisions.map((revision) => [revision.id, revision.revisionNumber]),
+    );
+    const revisionsToInsert: PlannedDocumentRevisionInsert[] = [];
+
+    for (const revision of sourceRevisions) {
+      if (existingRevisionIds.has(revision.id)) continue;
+      let targetRevisionNumber = revision.revisionNumber;
+      if (usedRevisionNumbers.has(targetRevisionNumber)) {
+        while (usedRevisionNumbers.has(nextRevisionNumber)) {
+          nextRevisionNumber += 1;
+        }
+        targetRevisionNumber = nextRevisionNumber;
+        nextRevisionNumber += 1;
+      }
+      usedRevisionNumbers.add(targetRevisionNumber);
+      targetRevisionNumberById.set(revision.id, targetRevisionNumber);
+
+      const revisionAdjustments: ImportAdjustment[] = [];
+      const targetCreatedByAgentId =
+        revision.createdByAgentId && targetAgentIds.has(revision.createdByAgentId) ? revision.createdByAgentId : null;
+      if (revision.createdByAgentId && !targetCreatedByAgentId) {
+        revisionAdjustments.push("clear_document_revision_agent");
+        incrementAdjustment(adjustmentCounts, "clear_document_revision_agent");
+      }
+
+      revisionsToInsert.push({
+        source: revision,
+        targetRevisionNumber,
+        targetCreatedByAgentId,
+        adjustments: revisionAdjustments,
+      });
+    }
+
+    const latestRevisionId = document.latestRevisionId ?? existingDocument?.latestRevisionId ?? null;
+    const latestRevisionNumber =
+      (latestRevisionId ? targetRevisionNumberById.get(latestRevisionId) : undefined)
+      ?? document.latestRevisionNumber
+      ?? existingDocument?.latestRevisionNumber
+      ?? 0;
+
+    if (!existingDocument) {
+      documentPlans.push({
+        source: document,
+        action: "insert",
+        targetCreatedByAgentId,
+        targetUpdatedByAgentId,
+        latestRevisionId,
+        latestRevisionNumber,
+        revisionsToInsert,
+        adjustments,
+      });
+      continue;
+    }
+
+    const documentAlreadyMatches =
+      existingDocument.key === document.key
+      && existingDocument.title === document.title
+      && existingDocument.format === document.format
+      && existingDocument.latestBody === document.latestBody
+      && (existingDocument.latestRevisionId ?? null) === latestRevisionId
+      && existingDocument.latestRevisionNumber === latestRevisionNumber
+      && (existingDocument.updatedByAgentId ?? null) === targetUpdatedByAgentId
+      && (existingDocument.updatedByUserId ?? null) === (document.updatedByUserId ?? null)
+      && sameDate(existingDocument.documentUpdatedAt, document.documentUpdatedAt)
+      && sameDate(existingDocument.linkUpdatedAt, document.linkUpdatedAt)
+      && revisionsToInsert.length === 0;
+
+    if (documentAlreadyMatches) {
+      documentPlans.push({ source: document, action: "skip_existing" });
+      continue;
+    }
+
+    documentPlans.push({
+      source: document,
+      action: "merge_existing",
+      targetCreatedByAgentId,
+      targetUpdatedByAgentId,
+      latestRevisionId,
+      latestRevisionNumber,
+      revisionsToInsert,
+      adjustments,
+    });
+  }
+
+  const sourceAttachments = input.sourceAttachments ?? [];
+  const targetAttachmentIds = new Set((input.targetAttachments ?? []).map((attachment) => attachment.id));
+  const attachmentPlans: Array<PlannedAttachmentInsert | PlannedAttachmentSkip> = [];
+  for (const attachment of sortAttachments(sourceAttachments)) {
+    if (targetAttachmentIds.has(attachment.id)) {
+      attachmentPlans.push({ source: attachment, action: "skip_existing" });
+      continue;
+    }
+    if (!issueIdsAvailableAfterImport.has(attachment.issueId)) {
+      attachmentPlans.push({ source: attachment, action: "skip_missing_parent" });
+      continue;
+    }
+
+    const adjustments: ImportAdjustment[] = [];
+    const targetCreatedByAgentId =
+      attachment.createdByAgentId && targetAgentIds.has(attachment.createdByAgentId)
+        ? attachment.createdByAgentId
+        : null;
+    if (attachment.createdByAgentId && !targetCreatedByAgentId) {
+      adjustments.push("clear_attachment_agent");
+      incrementAdjustment(adjustmentCounts, "clear_attachment_agent");
+    }
+
+    attachmentPlans.push({
+      source: attachment,
+      action: "insert",
+      targetIssueCommentId:
+        attachment.issueCommentId && commentIdsAvailableAfterImport.has(attachment.issueCommentId)
+          ? attachment.issueCommentId
+          : null,
+      targetCreatedByAgentId,
+      adjustments,
+    });
+  }
+
  const counts = {
    issuesToInsert: issuePlans.filter((plan) => plan.action === "insert").length,
    issuesExisting: issuePlans.filter((plan) => plan.action === "skip_existing").length,
@@ -331,6 +678,19 @@ export function buildWorktreeMergePlan(input: {
    commentsToInsert: commentPlans.filter((plan) => plan.action === "insert").length,
    commentsExisting: commentPlans.filter((plan) => plan.action === "skip_existing").length,
    commentsMissingParent: commentPlans.filter((plan) => plan.action === "skip_missing_parent").length,
+    documentsToInsert: documentPlans.filter((plan) => plan.action === "insert").length,
+    documentsToMerge: documentPlans.filter((plan) => plan.action === "merge_existing").length,
+    documentsExisting: documentPlans.filter((plan) => plan.action === "skip_existing").length,
+    documentsConflictingKey: documentPlans.filter((plan) => plan.action === "skip_conflicting_key").length,
+    documentsMissingParent: documentPlans.filter((plan) => plan.action === "skip_missing_parent").length,
+    documentRevisionsToInsert: documentPlans.reduce(
+      (sum, plan) =>
+        sum + (plan.action === "insert" || plan.action === "merge_existing" ? plan.revisionsToInsert.length : 0),
+      0,
+    ),
+    attachmentsToInsert: attachmentPlans.filter((plan) => plan.action === "insert").length,
+    attachmentsExisting: attachmentPlans.filter((plan) => plan.action === "skip_existing").length,
+    attachmentsMissingParent: attachmentPlans.filter((plan) => plan.action === "skip_missing_parent").length,
  };

  return {
@@ -341,6 +701,8 @@ export function buildWorktreeMergePlan(input: {
    scopes: input.scopes,
    issuePlans,
    commentPlans,
+    documentPlans,
+    attachmentPlans,
    counts,
    adjustments: adjustmentCounts,
  };
--- a/cli/src/commands/worktree.ts
+++ b/cli/src/commands/worktree.ts
@@ -3,6 +3,7 @@ import {
  copyFileSync,
  existsSync,
  mkdirSync,
+  promises as fsPromises,
  readdirSync,
  readFileSync,
  readlinkSync,
@@ -15,18 +16,23 @@ import os from "node:os";
 import path from "node:path";
 import { execFileSync } from "node:child_process";
 import { createServer } from "node:net";
+import { Readable } from "node:stream";
 import * as p from "@clack/prompts";
 import pc from "picocolors";
 import { and, eq, inArray, sql } from "drizzle-orm";
 import {
  applyPendingMigrations,
  agents,
+  assets,
  companies,
  createDb,
+  documentRevisions,
+  documents,
  ensurePostgresDatabase,
  formatDatabaseBackupResult,
  goals,
  heartbeatRuns,
+  issueAttachments,
  issueComments,
  issueDocuments,
  issues,
@@ -59,7 +65,13 @@ import {
 import {
  buildWorktreeMergePlan,
  parseWorktreeMergeScopes,
+  type IssueAttachmentRow,
+  type IssueDocumentRow,
+  type DocumentRevisionRow,
+  type PlannedAttachmentInsert,
  type PlannedCommentInsert,
+  type PlannedIssueDocumentInsert,
+  type PlannedIssueDocumentMerge,
  type PlannedIssueInsert,
 } from "./worktree-merge-history-lib.js";

@@ -181,6 +193,162 @@ function resolveWorktreeStartPoint(explicit?: string): string | undefined {
  return explicit ?? nonEmpty(process.env.PAPERCLIP_WORKTREE_START_POINT) ?? undefined;
 }

+type ConfiguredStorage = {
+  getObject(companyId: string, objectKey: string): Promise<Buffer>;
+  putObject(companyId: string, objectKey: string, body: Buffer, contentType: string): Promise<void>;
+};
+
+function assertStorageCompanyPrefix(companyId: string, objectKey: string): void {
+  if (!objectKey.startsWith(`${companyId}/`) || objectKey.includes("..")) {
+    throw new Error(`Invalid object key for company ${companyId}.`);
+  }
+}
+
+function normalizeStorageObjectKey(objectKey: string): string {
+  const normalized = objectKey.replace(/\\/g, "/").trim();
+  if (!normalized || normalized.startsWith("/")) {
+    throw new Error("Invalid object key.");
+  }
+  const parts = normalized.split("/").filter((part) => part.length > 0);
+  if (parts.length === 0 || parts.some((part) => part === "." || part === "..")) {
+    throw new Error("Invalid object key.");
+  }
+  return parts.join("/");
+}
+
+function resolveLocalStoragePath(baseDir: string, objectKey: string): string {
+  const resolved = path.resolve(baseDir, normalizeStorageObjectKey(objectKey));
+  const root = path.resolve(baseDir);
+  if (resolved !== root && !resolved.startsWith(`${root}${path.sep}`)) {
+    throw new Error("Invalid object key path.");
+  }
+  return resolved;
+}
+
+async function s3BodyToBuffer(body: unknown): Promise<Buffer> {
+  if (!body) {
+    throw new Error("Object not found.");
+  }
+  if (Buffer.isBuffer(body)) {
+    return body;
+  }
+  if (body instanceof Readable) {
+    return await streamToBuffer(body);
+  }
+
+  const candidate = body as {
+    transformToWebStream?: () => ReadableStream<Uint8Array>;
+    arrayBuffer?: () => Promise<ArrayBuffer>;
+  };
+  if (typeof candidate.transformToWebStream === "function") {
+    const webStream = candidate.transformToWebStream();
+    const reader = webStream.getReader();
+    const chunks: Uint8Array[] = [];
+    while (true) {
+      const { done, value } = await reader.read();
+      if (done) break;
+      if (value) chunks.push(value);
+    }
+    return Buffer.concat(chunks.map((chunk) => Buffer.from(chunk)));
+  }
+  if (typeof candidate.arrayBuffer === "function") {
+    return Buffer.from(await candidate.arrayBuffer());
+  }
+
+  throw new Error("Unsupported storage response body.");
+}
+
+function normalizeS3Prefix(prefix: string | undefined): string {
+  if (!prefix) return "";
+  return prefix.trim().replace(/^\/+/, "").replace(/\/+$/, "");
+}
+
+function buildS3ObjectKey(prefix: string, objectKey: string): string {
+  return prefix ? `${prefix}/${objectKey}` : objectKey;
+}
+
+const dynamicImport = new Function("specifier", "return import(specifier);") as (specifier: string) => Promise<any>;
+
+function createConfiguredStorageFromPaperclipConfig(config: PaperclipConfig): ConfiguredStorage {
+  if (config.storage.provider === "local_disk") {
+    const baseDir = expandHomePrefix(config.storage.localDisk.baseDir);
+    return {
+      async getObject(companyId: string, objectKey: string) {
+        assertStorageCompanyPrefix(companyId, objectKey);
+        return await fsPromises.readFile(resolveLocalStoragePath(baseDir, objectKey));
+      },
+      async putObject(companyId: string, objectKey: string, body: Buffer) {
+        assertStorageCompanyPrefix(companyId, objectKey);
+        const filePath = resolveLocalStoragePath(baseDir, objectKey);
+        await fsPromises.mkdir(path.dirname(filePath), { recursive: true });
+        await fsPromises.writeFile(filePath, body);
+      },
+    };
+  }
+
+  const prefix = normalizeS3Prefix(config.storage.s3.prefix);
+  let s3ClientPromise: Promise<any> | null = null;
+  async function getS3Client() {
+    if (!s3ClientPromise) {
+      s3ClientPromise = (async () => {
+        const sdk = await dynamicImport("@aws-sdk/client-s3");
+        return {
+          sdk,
+          client: new sdk.S3Client({
+            region: config.storage.s3.region,
+            endpoint: config.storage.s3.endpoint,
+            forcePathStyle: config.storage.s3.forcePathStyle,
+          }),
+        };
+      })();
+    }
+    return await s3ClientPromise;
+  }
+  const bucket = config.storage.s3.bucket;
+  return {
+    async getObject(companyId: string, objectKey: string) {
+      assertStorageCompanyPrefix(companyId, objectKey);
+      const { sdk, client } = await getS3Client();
+      const response = await client.send(
+        new sdk.GetObjectCommand({
+          Bucket: bucket,
+          Key: buildS3ObjectKey(prefix, objectKey),
+        }),
+      );
+      return await s3BodyToBuffer(response.Body);
+    },
+    async putObject(companyId: string, objectKey: string, body: Buffer, contentType: string) {
+      assertStorageCompanyPrefix(companyId, objectKey);
+      const { sdk, client } = await getS3Client();
+      await client.send(
+        new sdk.PutObjectCommand({
+          Bucket: bucket,
+          Key: buildS3ObjectKey(prefix, objectKey),
+          Body: body,
+          ContentType: contentType,
+          ContentLength: body.length,
+        }),
+      );
+    },
+  };
+}
+
+function openConfiguredStorage(configPath: string): ConfiguredStorage {
+  const config = readConfig(configPath);
+  if (!config) {
+    throw new Error(`Config not found at ${configPath}.`);
+  }
+  return createConfiguredStorageFromPaperclipConfig(config);
+}
+
+async function streamToBuffer(stream: NodeJS.ReadableStream): Promise<Buffer> {
+  const chunks: Buffer[] = [];
+  for await (const chunk of stream) {
+    chunks.push(Buffer.isBuffer(chunk) ? chunk : Buffer.from(chunk));
+  }
+  return Buffer.concat(chunks);
+}
+
 export function resolveWorktreeMakeTargetPath(name: string): string {
  return path.resolve(os.homedir(), resolveWorktreeMakeName(name));
 }
@@ -1244,7 +1412,6 @@ function renderMergePlan(plan: Awaited<ReturnType<typeof collectMergePlan>>["pla
  sourcePath: string;
  targetPath: string;
  unsupportedRunCount: number;
-  unsupportedDocumentCount: number;
 }): string {
  const terminalWidth = Math.max(60, process.stdout.columns ?? 100);
  const oneLine = (value: string) => value.replace(/\s+/g, " ").trim();
@@ -1292,6 +1459,21 @@ function renderMergePlan(plan: Awaited<ReturnType<typeof collectMergePlan>>["pla
    lines.push(`- skipped (missing parent): ${plan.counts.commentsMissingParent}`);
  }

+  lines.push("");
+  lines.push("Documents");
+  lines.push(`- insert: ${plan.counts.documentsToInsert}`);
+  lines.push(`- merge existing: ${plan.counts.documentsToMerge}`);
+  lines.push(`- already present: ${plan.counts.documentsExisting}`);
+  lines.push(`- skipped (conflicting key): ${plan.counts.documentsConflictingKey}`);
+  lines.push(`- skipped (missing parent): ${plan.counts.documentsMissingParent}`);
+  lines.push(`- revisions insert: ${plan.counts.documentRevisionsToInsert}`);
+
+  lines.push("");
+  lines.push("Attachments");
+  lines.push(`- insert: ${plan.counts.attachmentsToInsert}`);
+  lines.push(`- already present: ${plan.counts.attachmentsExisting}`);
+  lines.push(`- skipped (missing parent): ${plan.counts.attachmentsMissingParent}`);
+
  lines.push("");
  lines.push("Adjustments");
  lines.push(`- cleared assignee agents: ${plan.adjustments.clear_assignee_agent}`);
@@ -1299,12 +1481,14 @@ function renderMergePlan(plan: Awaited<ReturnType<typeof collectMergePlan>>["pla
  lines.push(`- cleared project workspaces: ${plan.adjustments.clear_project_workspace}`);
  lines.push(`- cleared goals: ${plan.adjustments.clear_goal}`);
  lines.push(`- cleared comment author agents: ${plan.adjustments.clear_author_agent}`);
+  lines.push(`- cleared document agents: ${plan.adjustments.clear_document_agent}`);
+  lines.push(`- cleared document revision agents: ${plan.adjustments.clear_document_revision_agent}`);
+  lines.push(`- cleared attachment author agents: ${plan.adjustments.clear_attachment_agent}`);
  lines.push(`- coerced in_progress to todo: ${plan.adjustments.coerce_in_progress_to_todo}`);

  lines.push("");
  lines.push("Not imported in this phase");
  lines.push(`- heartbeat runs: ${extras.unsupportedRunCount}`);
-  lines.push(`- issue documents: ${extras.unsupportedDocumentCount}`);
  lines.push("");
  lines.push("Identifiers shown above are provisional preview values. `--apply` reserves fresh issue numbers at write time.");

@@ -1319,7 +1503,25 @@ async function collectMergePlan(input: {
  projectIdOverrides?: Record<string, string | null | undefined>;
 }) {
  const companyId = input.company.id;
-  const [targetCompanyRow, sourceIssuesRows, targetIssuesRows, sourceCommentsRows, targetCommentsRows, sourceProjectsRows, targetProjectsRows, targetAgentsRows, targetProjectWorkspaceRows, targetGoalsRows, runCountRows, documentCountRows] = await Promise.all([
+  const [
+    targetCompanyRow,
+    sourceIssuesRows,
+    targetIssuesRows,
+    sourceCommentsRows,
+    targetCommentsRows,
+    sourceIssueDocumentsRows,
+    targetIssueDocumentsRows,
+    sourceDocumentRevisionRows,
+    targetDocumentRevisionRows,
+    sourceAttachmentRows,
+    targetAttachmentRows,
+    sourceProjectsRows,
+    targetProjectsRows,
+    targetAgentsRows,
+    targetProjectWorkspaceRows,
+    targetGoalsRows,
+    runCountRows,
+  ] = await Promise.all([
    input.targetDb
      .select({
        issueCounter: companies.issueCounter,
@@ -1341,12 +1543,140 @@ async function collectMergePlan(input: {
        .from(issueComments)
        .where(eq(issueComments.companyId, companyId))
      : Promise.resolve([]),
-    input.scopes.includes("comments")
-      ? input.targetDb
-        .select()
-        .from(issueComments)
-        .where(eq(issueComments.companyId, companyId))
-      : Promise.resolve([]),
+    input.targetDb
+      .select()
+      .from(issueComments)
+      .where(eq(issueComments.companyId, companyId)),
+    input.sourceDb
+      .select({
+        id: issueDocuments.id,
+        companyId: issueDocuments.companyId,
+        issueId: issueDocuments.issueId,
+        documentId: issueDocuments.documentId,
+        key: issueDocuments.key,
+        linkCreatedAt: issueDocuments.createdAt,
+        linkUpdatedAt: issueDocuments.updatedAt,
+        title: documents.title,
+        format: documents.format,
+        latestBody: documents.latestBody,
+        latestRevisionId: documents.latestRevisionId,
+        latestRevisionNumber: documents.latestRevisionNumber,
+        createdByAgentId: documents.createdByAgentId,
+        createdByUserId: documents.createdByUserId,
+        updatedByAgentId: documents.updatedByAgentId,
+        updatedByUserId: documents.updatedByUserId,
+        documentCreatedAt: documents.createdAt,
+        documentUpdatedAt: documents.updatedAt,
+      })
+      .from(issueDocuments)
+      .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+      .innerJoin(issues, eq(issueDocuments.issueId, issues.id))
+      .where(eq(issues.companyId, companyId)),
+    input.targetDb
+      .select({
+        id: issueDocuments.id,
+        companyId: issueDocuments.companyId,
+        issueId: issueDocuments.issueId,
+        documentId: issueDocuments.documentId,
+        key: issueDocuments.key,
+        linkCreatedAt: issueDocuments.createdAt,
+        linkUpdatedAt: issueDocuments.updatedAt,
+        title: documents.title,
+        format: documents.format,
+        latestBody: documents.latestBody,
+        latestRevisionId: documents.latestRevisionId,
+        latestRevisionNumber: documents.latestRevisionNumber,
+        createdByAgentId: documents.createdByAgentId,
+        createdByUserId: documents.createdByUserId,
+        updatedByAgentId: documents.updatedByAgentId,
+        updatedByUserId: documents.updatedByUserId,
+        documentCreatedAt: documents.createdAt,
+        documentUpdatedAt: documents.updatedAt,
+      })
+      .from(issueDocuments)
+      .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+      .innerJoin(issues, eq(issueDocuments.issueId, issues.id))
+      .where(eq(issues.companyId, companyId)),
+    input.sourceDb
+      .select({
+        id: documentRevisions.id,
+        companyId: documentRevisions.companyId,
+        documentId: documentRevisions.documentId,
+        revisionNumber: documentRevisions.revisionNumber,
+        body: documentRevisions.body,
+        changeSummary: documentRevisions.changeSummary,
+        createdByAgentId: documentRevisions.createdByAgentId,
+        createdByUserId: documentRevisions.createdByUserId,
+        createdAt: documentRevisions.createdAt,
+      })
+      .from(documentRevisions)
+      .innerJoin(issueDocuments, eq(documentRevisions.documentId, issueDocuments.documentId))
+      .innerJoin(issues, eq(issueDocuments.issueId, issues.id))
+      .where(eq(issues.companyId, companyId)),
+    input.targetDb
+      .select({
+        id: documentRevisions.id,
+        companyId: documentRevisions.companyId,
+        documentId: documentRevisions.documentId,
+        revisionNumber: documentRevisions.revisionNumber,
+        body: documentRevisions.body,
+        changeSummary: documentRevisions.changeSummary,
+        createdByAgentId: documentRevisions.createdByAgentId,
+        createdByUserId: documentRevisions.createdByUserId,
+        createdAt: documentRevisions.createdAt,
+      })
+      .from(documentRevisions)
+      .innerJoin(issueDocuments, eq(documentRevisions.documentId, issueDocuments.documentId))
+      .innerJoin(issues, eq(issueDocuments.issueId, issues.id))
+      .where(eq(issues.companyId, companyId)),
+    input.sourceDb
+      .select({
+        id: issueAttachments.id,
+        companyId: issueAttachments.companyId,
+        issueId: issueAttachments.issueId,
+        issueCommentId: issueAttachments.issueCommentId,
+        assetId: issueAttachments.assetId,
+        provider: assets.provider,
+        objectKey: assets.objectKey,
+        contentType: assets.contentType,
+        byteSize: assets.byteSize,
+        sha256: assets.sha256,
+        originalFilename: assets.originalFilename,
+        createdByAgentId: assets.createdByAgentId,
+        createdByUserId: assets.createdByUserId,
+        assetCreatedAt: assets.createdAt,
+        assetUpdatedAt: assets.updatedAt,
+        attachmentCreatedAt: issueAttachments.createdAt,
+        attachmentUpdatedAt: issueAttachments.updatedAt,
+      })
+      .from(issueAttachments)
+      .innerJoin(assets, eq(issueAttachments.assetId, assets.id))
+      .innerJoin(issues, eq(issueAttachments.issueId, issues.id))
+      .where(eq(issues.companyId, companyId)),
+    input.targetDb
+      .select({
+        id: issueAttachments.id,
+        companyId: issueAttachments.companyId,
+        issueId: issueAttachments.issueId,
+        issueCommentId: issueAttachments.issueCommentId,
+        assetId: issueAttachments.assetId,
+        provider: assets.provider,
+        objectKey: assets.objectKey,
+        contentType: assets.contentType,
+        byteSize: assets.byteSize,
+        sha256: assets.sha256,
+        originalFilename: assets.originalFilename,
+        createdByAgentId: assets.createdByAgentId,
+        createdByUserId: assets.createdByUserId,
+        assetCreatedAt: assets.createdAt,
+        assetUpdatedAt: assets.updatedAt,
+        attachmentCreatedAt: issueAttachments.createdAt,
+        attachmentUpdatedAt: issueAttachments.updatedAt,
+      })
+      .from(issueAttachments)
+      .innerJoin(assets, eq(issueAttachments.assetId, assets.id))
+      .innerJoin(issues, eq(issueAttachments.issueId, issues.id))
+      .where(eq(issues.companyId, companyId)),
    input.sourceDb
      .select()
      .from(projects)
@@ -1371,11 +1701,6 @@ async function collectMergePlan(input: {
      .select({ count: sql<number>`count(*)::int` })
      .from(heartbeatRuns)
      .where(eq(heartbeatRuns.companyId, companyId)),
-    input.sourceDb
-      .select({ count: sql<number>`count(*)::int` })
-      .from(issueDocuments)
-      .innerJoin(issues, eq(issueDocuments.issueId, issues.id))
-      .where(eq(issues.companyId, companyId)),
  ]);

  if (!targetCompanyRow) {
@@ -1392,6 +1717,12 @@ async function collectMergePlan(input: {
    targetIssues: targetIssuesRows,
    sourceComments: sourceCommentsRows,
    targetComments: targetCommentsRows,
+    sourceDocuments: sourceIssueDocumentsRows as IssueDocumentRow[],
+    targetDocuments: targetIssueDocumentsRows as IssueDocumentRow[],
+    sourceDocumentRevisions: sourceDocumentRevisionRows as DocumentRevisionRow[],
+    targetDocumentRevisions: targetDocumentRevisionRows as DocumentRevisionRow[],
+    sourceAttachments: sourceAttachmentRows as IssueAttachmentRow[],
+    targetAttachments: targetAttachmentRows as IssueAttachmentRow[],
    targetAgents: targetAgentsRows,
    targetProjects: targetProjectsRows,
    targetProjectWorkspaces: targetProjectWorkspaceRows,
@@ -1404,7 +1735,6 @@ async function collectMergePlan(input: {
    sourceProjects: sourceProjectsRows,
    targetProjects: targetProjectsRows,
    unsupportedRunCount: runCountRows[0]?.count ?? 0,
-    unsupportedDocumentCount: documentCountRows[0]?.count ?? 0,
  };
 }

@@ -1575,6 +1905,8 @@ async function promptForSourceEndpoint(excludeWorktreePath?: string): Promise<Re
 }

 async function applyMergePlan(input: {
+  sourceStorage: ConfiguredStorage;
+  targetStorage: ConfiguredStorage;
  targetDb: ClosableDb;
  company: ResolvedMergeCompany;
  plan: Awaited<ReturnType<typeof collectMergePlan>>["plan"];
@@ -1608,6 +1940,7 @@ async function applyMergePlan(input: {
    }

    const insertedIssueIdentifiers = new Map<string, string>();
+    let insertedIssues = 0;
    for (const issue of issueInserts) {
      const issueNumber = nextIssueNumber;
      nextIssueNumber += 1;
@@ -1647,6 +1980,7 @@ async function applyMergePlan(input: {
        createdAt: issue.source.createdAt,
        updatedAt: issue.source.updatedAt,
      });
+      insertedIssues += 1;
    }

    const commentCandidates = input.plan.commentPlans.filter(
@@ -1663,6 +1997,7 @@ async function applyMergePlan(input: {
      )
      : new Set<string>();

+    let insertedComments = 0;
    for (const comment of commentCandidates) {
      if (existingCommentIds.has(comment.source.id)) continue;
      const parentExists = await tx
@@ -1681,11 +2016,199 @@ async function applyMergePlan(input: {
        createdAt: comment.source.createdAt,
        updatedAt: comment.source.updatedAt,
      });
+      insertedComments += 1;
+    }
+
+    const documentCandidates = input.plan.documentPlans.filter(
+      (plan): plan is PlannedIssueDocumentInsert | PlannedIssueDocumentMerge =>
+        plan.action === "insert" || plan.action === "merge_existing",
+    );
+    let insertedDocuments = 0;
+    let mergedDocuments = 0;
+    let insertedDocumentRevisions = 0;
+    for (const documentPlan of documentCandidates) {
+      const parentExists = await tx
+        .select({ id: issues.id })
+        .from(issues)
+        .where(and(eq(issues.id, documentPlan.source.issueId), eq(issues.companyId, companyId)))
+        .then((rows) => rows[0] ?? null);
+      if (!parentExists) continue;
+
+      const conflictingKeyDocument = await tx
+        .select({ documentId: issueDocuments.documentId })
+        .from(issueDocuments)
+        .where(and(eq(issueDocuments.issueId, documentPlan.source.issueId), eq(issueDocuments.key, documentPlan.source.key)))
+        .then((rows) => rows[0] ?? null);
+      if (
+        conflictingKeyDocument
+        && conflictingKeyDocument.documentId !== documentPlan.source.documentId
+      ) {
+        continue;
+      }
+
+      const existingDocument = await tx
+        .select({ id: documents.id })
+        .from(documents)
+        .where(eq(documents.id, documentPlan.source.documentId))
+        .then((rows) => rows[0] ?? null);
+
+      if (!existingDocument) {
+        await tx.insert(documents).values({
+          id: documentPlan.source.documentId,
+          companyId,
+          title: documentPlan.source.title,
+          format: documentPlan.source.format,
+          latestBody: documentPlan.source.latestBody,
+          latestRevisionId: documentPlan.latestRevisionId,
+          latestRevisionNumber: documentPlan.latestRevisionNumber,
+          createdByAgentId: documentPlan.targetCreatedByAgentId,
+          createdByUserId: documentPlan.source.createdByUserId,
+          updatedByAgentId: documentPlan.targetUpdatedByAgentId,
+          updatedByUserId: documentPlan.source.updatedByUserId,
+          createdAt: documentPlan.source.documentCreatedAt,
+          updatedAt: documentPlan.source.documentUpdatedAt,
+        });
+        await tx.insert(issueDocuments).values({
+          id: documentPlan.source.id,
+          companyId,
+          issueId: documentPlan.source.issueId,
+          documentId: documentPlan.source.documentId,
+          key: documentPlan.source.key,
+          createdAt: documentPlan.source.linkCreatedAt,
+          updatedAt: documentPlan.source.linkUpdatedAt,
+        });
+        insertedDocuments += 1;
+      } else {
+        const existingLink = await tx
+          .select({ id: issueDocuments.id })
+          .from(issueDocuments)
+          .where(eq(issueDocuments.documentId, documentPlan.source.documentId))
+          .then((rows) => rows[0] ?? null);
+        if (!existingLink) {
+          await tx.insert(issueDocuments).values({
+            id: documentPlan.source.id,
+            companyId,
+            issueId: documentPlan.source.issueId,
+            documentId: documentPlan.source.documentId,
+            key: documentPlan.source.key,
+            createdAt: documentPlan.source.linkCreatedAt,
+            updatedAt: documentPlan.source.linkUpdatedAt,
+          });
+        } else {
+          await tx
+            .update(issueDocuments)
+            .set({
+              issueId: documentPlan.source.issueId,
+              key: documentPlan.source.key,
+              updatedAt: documentPlan.source.linkUpdatedAt,
+            })
+            .where(eq(issueDocuments.documentId, documentPlan.source.documentId));
+        }
+
+        await tx
+          .update(documents)
+          .set({
+            title: documentPlan.source.title,
+            format: documentPlan.source.format,
+            latestBody: documentPlan.source.latestBody,
+            latestRevisionId: documentPlan.latestRevisionId,
+            latestRevisionNumber: documentPlan.latestRevisionNumber,
+            updatedByAgentId: documentPlan.targetUpdatedByAgentId,
+            updatedByUserId: documentPlan.source.updatedByUserId,
+            updatedAt: documentPlan.source.documentUpdatedAt,
+          })
+          .where(eq(documents.id, documentPlan.source.documentId));
+        mergedDocuments += 1;
+      }
+
+      const existingRevisionIds = new Set(
+        (
+          await tx
+            .select({ id: documentRevisions.id })
+            .from(documentRevisions)
+            .where(eq(documentRevisions.documentId, documentPlan.source.documentId))
+        ).map((row) => row.id),
+      );
+      for (const revisionPlan of documentPlan.revisionsToInsert) {
+        if (existingRevisionIds.has(revisionPlan.source.id)) continue;
+        await tx.insert(documentRevisions).values({
+          id: revisionPlan.source.id,
+          companyId,
+          documentId: documentPlan.source.documentId,
+          revisionNumber: revisionPlan.targetRevisionNumber,
+          body: revisionPlan.source.body,
+          changeSummary: revisionPlan.source.changeSummary,
+          createdByAgentId: revisionPlan.targetCreatedByAgentId,
+          createdByUserId: revisionPlan.source.createdByUserId,
+          createdAt: revisionPlan.source.createdAt,
+        });
+        insertedDocumentRevisions += 1;
+      }
+    }
+
+    const attachmentCandidates = input.plan.attachmentPlans.filter(
+      (plan): plan is PlannedAttachmentInsert => plan.action === "insert",
+    );
+    const existingAttachmentIds = new Set(
+      (
+        await tx
+          .select({ id: issueAttachments.id })
+          .from(issueAttachments)
+          .where(eq(issueAttachments.companyId, companyId))
+      ).map((row) => row.id),
+    );
+    let insertedAttachments = 0;
+    for (const attachment of attachmentCandidates) {
+      if (existingAttachmentIds.has(attachment.source.id)) continue;
+      const parentExists = await tx
+        .select({ id: issues.id })
+        .from(issues)
+        .where(and(eq(issues.id, attachment.source.issueId), eq(issues.companyId, companyId)))
+        .then((rows) => rows[0] ?? null);
+      if (!parentExists) continue;
+
+      const body = await input.sourceStorage.getObject(companyId, attachment.source.objectKey);
+      await input.targetStorage.putObject(
+        companyId,
+        attachment.source.objectKey,
+        body,
+        attachment.source.contentType,
+      );
+
+      await tx.insert(assets).values({
+        id: attachment.source.assetId,
+        companyId,
+        provider: attachment.source.provider,
+        objectKey: attachment.source.objectKey,
+        contentType: attachment.source.contentType,
+        byteSize: attachment.source.byteSize,
+        sha256: attachment.source.sha256,
+        originalFilename: attachment.source.originalFilename,
+        createdByAgentId: attachment.targetCreatedByAgentId,
+        createdByUserId: attachment.source.createdByUserId,
+        createdAt: attachment.source.assetCreatedAt,
+        updatedAt: attachment.source.assetUpdatedAt,
+      });
+
+      await tx.insert(issueAttachments).values({
+        id: attachment.source.id,
+        companyId,
+        issueId: attachment.source.issueId,
+        assetId: attachment.source.assetId,
+        issueCommentId: attachment.targetIssueCommentId,
+        createdAt: attachment.source.attachmentCreatedAt,
+        updatedAt: attachment.source.attachmentUpdatedAt,
+      });
+      insertedAttachments += 1;
    }

    return {
-      insertedIssues: issueInserts.length,
-      insertedComments: commentCandidates.filter((comment) => !existingCommentIds.has(comment.source.id)).length,
+      insertedIssues,
+      insertedComments,
+      insertedDocuments,
+      mergedDocuments,
+      insertedDocumentRevisions,
+      insertedAttachments,
      insertedIssueIdentifiers,
    };
  });
@@ -1716,6 +2239,8 @@ export async function worktreeMergeHistoryCommand(sourceArg: string | undefined,
  const scopes = parseWorktreeMergeScopes(opts.scope);
  const sourceHandle = await openConfiguredDb(sourceEndpoint.configPath);
  const targetHandle = await openConfiguredDb(targetEndpoint.configPath);
+  const sourceStorage = openConfiguredStorage(sourceEndpoint.configPath);
+  const targetStorage = openConfiguredStorage(targetEndpoint.configPath);

  try {
    const company = await resolveMergeCompany({
@@ -1750,7 +2275,6 @@ export async function worktreeMergeHistoryCommand(sourceArg: string | undefined,
      sourcePath: `${sourceEndpoint.label} (${sourceEndpoint.rootPath})`,
      targetPath: `${targetEndpoint.label} (${targetEndpoint.rootPath})`,
      unsupportedRunCount: collected.unsupportedRunCount,
-      unsupportedDocumentCount: collected.unsupportedDocumentCount,
    }));

    if (!opts.apply) {
@@ -1769,13 +2293,15 @@ export async function worktreeMergeHistoryCommand(sourceArg: string | undefined,
    }

    const applied = await applyMergePlan({
+      sourceStorage,
+      targetStorage,
      targetDb: targetHandle.db,
      company,
      plan: collected.plan,
    });
    p.outro(
      pc.green(
-        `Imported ${applied.insertedIssues} issues and ${applied.insertedComments} comments into ${company.issuePrefix}.`,
+        `Imported ${applied.insertedIssues} issues, ${applied.insertedComments} comments, ${applied.insertedDocuments} documents (${applied.insertedDocumentRevisions} revisions, ${applied.mergedDocuments} merged), and ${applied.insertedAttachments} attachments into ${company.issuePrefix}.`,
      ),
    );
  } finally {