Chore(deps): Bump the small-changes group across 1 directory with 7 updates

Bumps the small-changes group with 7 updates in the / directory: | Package | From | To | | --- | --- | --- | | [filelock](https://github.com/tox-dev/py-filelock) | `3.19.1` | `3.20.0` | | [nltk](https://github.com/nltk/nltk) | `3.9.1` | `3.9.2` | | [mkdocs-material](https://github.com/squidfunk/mkdocs-material) | `9.6.20` | `9.6.21` | | [pytest-env](https://github.com/pytest-dev/pytest-env) | `1.1.5` | `1.2.0` | | [pytest-rerunfailures](https://github.com/pytest-dev/pytest-rerunfailures) | `16.0.1` | `16.1` | | [pre-commit-uv](https://github.com/tox-dev/pre-commit-uv) | `4.1.5` | `4.2.0` | | [ruff](https://github.com/astral-sh/ruff) | `0.13.2` | `0.14.0` | Updates `filelock` from 3.19.1 to 3.20.0 - [Release notes](https://github.com/tox-dev/py-filelock/releases) - [Changelog](https://github.com/tox-dev/filelock/blob/main/docs/changelog.rst) - [Commits](https://github.com/tox-dev/py-filelock/compare/3.19.1...3.20.0) Updates `nltk` from 3.9.1 to 3.9.2 - [Changelog](https://github.com/nltk/nltk/blob/develop/ChangeLog) - [Commits](https://github.com/nltk/nltk/compare/3.9.1...3.9.2) Updates `mkdocs-material` from 9.6.20 to 9.6.21 - [Release notes](https://github.com/squidfunk/mkdocs-material/releases) - [Changelog](https://github.com/squidfunk/mkdocs-material/blob/master/CHANGELOG) - [Commits](https://github.com/squidfunk/mkdocs-material/compare/9.6.20...9.6.21) Updates `pytest-env` from 1.1.5 to 1.2.0 - [Release notes](https://github.com/pytest-dev/pytest-env/releases) - [Commits](https://github.com/pytest-dev/pytest-env/compare/1.1.5...1.2.0) Updates `pytest-rerunfailures` from 16.0.1 to 16.1 - [Changelog](https://github.com/pytest-dev/pytest-rerunfailures/blob/master/CHANGES.rst) - [Commits](https://github.com/pytest-dev/pytest-rerunfailures/compare/16.0.1...16.1) Updates `pre-commit-uv` from 4.1.5 to 4.2.0 - [Release notes](https://github.com/tox-dev/pre-commit-uv/releases) - [Commits](https://github.com/tox-dev/pre-commit-uv/compare/4.1.5...4.2.0) Updates `ruff` from 0.13.2 to 0.14.0 - [Release notes](https://github.com/astral-sh/ruff/releases) - [Changelog](https://github.com/astral-sh/ruff/blob/main/CHANGELOG.md) - [Commits](https://github.com/astral-sh/ruff/compare/0.13.2...0.14.0) --- updated-dependencies: - dependency-name: filelock dependency-version: 3.20.0 dependency-type: direct:production update-type: version-update:semver-minor dependency-group: small-changes - dependency-name: nltk dependency-version: 3.9.2 dependency-type: direct:production update-type: version-update:semver-patch dependency-group: small-changes - dependency-name: mkdocs-material dependency-version: 9.6.21 dependency-type: direct:production update-type: version-update:semver-patch dependency-group: small-changes - dependency-name: pytest-env dependency-version: 1.2.0 dependency-type: direct:production update-type: version-update:semver-minor dependency-group: small-changes - dependency-name: pytest-rerunfailures dependency-version: '16.1' dependency-type: direct:production update-type: version-update:semver-minor dependency-group: small-changes - dependency-name: pre-commit-uv dependency-version: 4.2.0 dependency-type: direct:production update-type: version-update:semver-minor dependency-group: small-changes - dependency-name: ruff dependency-version: 0.14.0 dependency-type: direct:production update-type: version-update:semver-minor dependency-group: small-changes ... Signed-off-by: dependabot[bot] <support@github.com>
Feature: add support for emailing multiple documents (#10666 )
2025-10-14 02:36:10 -05:00 · 2025-10-13 20:27:03 +00:00 · 2025-10-13 13:16:43 -07:00
20 changed files with 622 additions and 154 deletions
--- a/docker/compose/docker-compose.ci-test.yml
+++ b/docker/compose/docker-compose.ci-test.yml
@@ -4,7 +4,7 @@
 # correct networking for the tests
 services:
  gotenberg:
-    image: docker.io/gotenberg/gotenberg:8.24
+    image: docker.io/gotenberg/gotenberg:8.23
    hostname: gotenberg
    container_name: gotenberg
    network_mode: host
--- a/docker/compose/docker-compose.mariadb-tika.yml
+++ b/docker/compose/docker-compose.mariadb-tika.yml
@@ -72,7 +72,7 @@ services:
      PAPERLESS_TIKA_GOTENBERG_ENDPOINT: http://gotenberg:3000
      PAPERLESS_TIKA_ENDPOINT: http://tika:9998
  gotenberg:
-    image: docker.io/gotenberg/gotenberg:8.24
+    image: docker.io/gotenberg/gotenberg:8.23
    restart: unless-stopped
    # The gotenberg chromium route is used to convert .eml files. We do not
    # want to allow external content like tracking pixels or even javascript.
--- a/docker/compose/docker-compose.postgres-tika.yml
+++ b/docker/compose/docker-compose.postgres-tika.yml
@@ -66,7 +66,7 @@ services:
      PAPERLESS_TIKA_GOTENBERG_ENDPOINT: http://gotenberg:3000
      PAPERLESS_TIKA_ENDPOINT: http://tika:9998
  gotenberg:
-    image: docker.io/gotenberg/gotenberg:8.24
+    image: docker.io/gotenberg/gotenberg:8.23
    restart: unless-stopped
    # The gotenberg chromium route is used to convert .eml files. We do not
    # want to allow external content like tracking pixels or even javascript.
--- a/docker/compose/docker-compose.sqlite-tika.yml
+++ b/docker/compose/docker-compose.sqlite-tika.yml
@@ -55,7 +55,7 @@ services:
      PAPERLESS_TIKA_GOTENBERG_ENDPOINT: http://gotenberg:3000
      PAPERLESS_TIKA_ENDPOINT: http://tika:9998
  gotenberg:
-    image: docker.io/gotenberg/gotenberg:8.24
+    image: docker.io/gotenberg/gotenberg:8.23
    restart: unless-stopped
    # The gotenberg chromium route is used to convert .eml files. We do not
    # want to allow external content like tracking pixels or even javascript.
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -42,7 +42,7 @@ dependencies = [
  "drf-spectacular~=0.28",
  "drf-spectacular-sidecar~=2025.9.1",
  "drf-writable-nested~=0.7.1",
-  "filelock~=3.19.1",
+  "filelock~=3.20.0",
  "flower~=2.0.1",
  "gotenberg-client~=0.11.0",
  "httpx-oauth~=0.16",
@@ -115,8 +115,8 @@ testing = [

 lint = [
  "pre-commit~=4.3.0",
-  "pre-commit-uv~=4.1.3",
-  "ruff~=0.13.0",
+  "pre-commit-uv~=4.2.0",
+  "ruff~=0.14.0",
 ]

 typing = [
--- a/src-ui/src/app/components/common/email-document-dialog/email-document-dialog.component.html
+++ b/src-ui/src/app/components/common/email-document-dialog/email-document-dialog.component.html
@@ -1,5 +1,9 @@
 <div class="modal-header">
-    <h4 class="modal-title" id="modal-basic-title">{{title}}</h4>
+    <h4 class="modal-title" id="modal-basic-title" i18n>{
+      documentIds.length,
+      plural,
+      =1 {Email Document} other {Email {{documentIds.length}} Documents}
+    }</h4>
    <button type="button" class="btn-close" aria-label="Close" (click)="close()"></button>
 </div>
 <div class="modal-body">
@@ -22,11 +26,14 @@
            <input class="form-check-input mt-0 me-2" type="checkbox" role="switch" id="useArchiveVersion" [disabled]="!hasArchiveVersion" [(ngModel)]="useArchiveVersion">
            <label class="form-check-label w-100 text-start" for="useArchiveVersion" i18n>Use archive version</label>
        </div>
-        <button type="submit" class="btn btn-outline-primary" (click)="emailDocument()" [disabled]="loading || emailAddress.length === 0 || emailMessage.length === 0 || emailSubject.length === 0">
+        <button type="submit" class="btn btn-outline-primary" (click)="emailDocuments()" [disabled]="loading || emailAddress.length === 0 || emailMessage.length === 0 || emailSubject.length === 0">
            @if (loading) {
                <div class="spinner-border spinner-border-sm me-2" role="status"></div>
            }
            <ng-container i18n>Send email</ng-container>
        </button>
    </div>
+    <div class="text-light fst-italic small mt-2">
+        <ng-container i18n>Some email servers may reject messages with large attachments.</ng-container>
+    </div>
 </div>
--- a/src-ui/src/app/components/common/email-document-dialog/email-document-dialog.component.spec.ts
+++ b/src-ui/src/app/components/common/email-document-dialog/email-document-dialog.component.spec.ts
@@ -36,31 +36,59 @@ describe('EmailDocumentDialogComponent', () => {
    documentService = TestBed.inject(DocumentService)
    toastService = TestBed.inject(ToastService)
    component = fixture.componentInstance
+    component.documentIds = [1]
    fixture.detectChanges()
  })

  it('should set hasArchiveVersion and useArchiveVersion', () => {
    expect(component.hasArchiveVersion).toBeTruthy()
+    expect(component.useArchiveVersion).toBeTruthy()
+
    component.hasArchiveVersion = false
    expect(component.hasArchiveVersion).toBeFalsy()
    expect(component.useArchiveVersion).toBeFalsy()
  })

-  it('should support sending document via email, showing error if needed', () => {
+  it('should support sending single document via email, showing error if needed', () => {
    const toastErrorSpy = jest.spyOn(toastService, 'showError')
    const toastSuccessSpy = jest.spyOn(toastService, 'showInfo')
+    component.documentIds = [1]
    component.emailAddress = 'hello@paperless-ngx.com'
    component.emailSubject = 'Hello'
    component.emailMessage = 'World'
    jest
-      .spyOn(documentService, 'emailDocument')
+      .spyOn(documentService, 'emailDocuments')
      .mockReturnValue(throwError(() => new Error('Unable to email document')))
-    component.emailDocument()
-    expect(toastErrorSpy).toHaveBeenCalled()
+    component.emailDocuments()
+    expect(toastErrorSpy).toHaveBeenCalledWith(
+      'Error emailing document',
+      expect.any(Error)
+    )

-    jest.spyOn(documentService, 'emailDocument').mockReturnValue(of(true))
-    component.emailDocument()
-    expect(toastSuccessSpy).toHaveBeenCalled()
+    jest.spyOn(documentService, 'emailDocuments').mockReturnValue(of(true))
+    component.emailDocuments()
+    expect(toastSuccessSpy).toHaveBeenCalledWith('Email sent')
+  })
+
+  it('should support sending multiple documents via email, showing appropriate messages', () => {
+    const toastErrorSpy = jest.spyOn(toastService, 'showError')
+    const toastSuccessSpy = jest.spyOn(toastService, 'showInfo')
+    component.documentIds = [1, 2, 3]
+    component.emailAddress = 'hello@paperless-ngx.com'
+    component.emailSubject = 'Hello'
+    component.emailMessage = 'World'
+    jest
+      .spyOn(documentService, 'emailDocuments')
+      .mockReturnValue(throwError(() => new Error('Unable to email documents')))
+    component.emailDocuments()
+    expect(toastErrorSpy).toHaveBeenCalledWith(
+      'Error emailing documents',
+      expect.any(Error)
+    )
+
+    jest.spyOn(documentService, 'emailDocuments').mockReturnValue(of(true))
+    component.emailDocuments()
+    expect(toastSuccessSpy).toHaveBeenCalledWith('Email sent')
  })

  it('should close the dialog', () => {
--- a/src-ui/src/app/components/common/email-document-dialog/email-document-dialog.component.ts
+++ b/src-ui/src/app/components/common/email-document-dialog/email-document-dialog.component.ts
@@ -18,10 +18,7 @@ export class EmailDocumentDialogComponent extends LoadingComponentWithPermission
  private toastService = inject(ToastService)

  @Input()
-  title = $localize`Email Document`
-
-  @Input()
-  documentId: number
+  documentIds: number[]

  private _hasArchiveVersion: boolean = true

@@ -46,11 +43,11 @@ export class EmailDocumentDialogComponent extends LoadingComponentWithPermission
    this.loading = false
  }

-  public emailDocument() {
+  public emailDocuments() {
    this.loading = true
    this.documentService
-      .emailDocument(
-        this.documentId,
+      .emailDocuments(
+        this.documentIds,
        this.emailAddress,
        this.emailSubject,
        this.emailMessage,
@@ -67,7 +64,11 @@ export class EmailDocumentDialogComponent extends LoadingComponentWithPermission
        },
        error: (e) => {
          this.loading = false
-          this.toastService.showError($localize`Error emailing document`, e)
+          const errorMessage =
+            this.documentIds.length > 1
+              ? $localize`Error emailing documents`
+              : $localize`Error emailing document`
+          this.toastService.showError(errorMessage, e)
        },
      })
  }
--- a/src-ui/src/app/components/document-detail/document-detail.component.ts
+++ b/src-ui/src/app/components/document-detail/document-detail.component.ts
@@ -1481,7 +1481,7 @@ export class DocumentDetailComponent
    const modal = this.modalService.open(EmailDocumentDialogComponent, {
      backdrop: 'static',
    })
-    modal.componentInstance.documentId = this.document.id
+    modal.componentInstance.documentIds = [this.document.id]
    modal.componentInstance.hasArchiveVersion =
      !!this.document?.archived_file_name
  }
--- a/src-ui/src/app/components/document-list/bulk-editor/bulk-editor.component.html
+++ b/src-ui/src/app/components/document-list/bulk-editor/bulk-editor.component.html
@@ -96,6 +96,9 @@
          <button ngbDropdownItem (click)="mergeSelected()" [disabled]="!userCanAdd || list.selected.size < 2">
            <i-bs name="journals"></i-bs>&nbsp;<ng-container i18n>Merge</ng-container>
          </button>
+          <button ngbDropdownItem (click)="emailSelected()" [disabled]="!userCanEdit">
+            <i-bs name="envelope"></i-bs>&nbsp;<ng-container i18n>Email</ng-container>
+          </button>
        </div>
      </div>
    </div>
--- a/src-ui/src/app/components/document-list/bulk-editor/bulk-editor.component.ts
+++ b/src-ui/src/app/components/document-list/bulk-editor/bulk-editor.component.ts
@@ -46,6 +46,7 @@ import { DocumentTypeEditDialogComponent } from '../../common/edit-dialog/docume
 import { EditDialogMode } from '../../common/edit-dialog/edit-dialog.component'
 import { StoragePathEditDialogComponent } from '../../common/edit-dialog/storage-path-edit-dialog/storage-path-edit-dialog.component'
 import { TagEditDialogComponent } from '../../common/edit-dialog/tag-edit-dialog/tag-edit-dialog.component'
+import { EmailDocumentDialogComponent } from '../../common/email-document-dialog/email-document-dialog.component'
 import {
  ChangedItems,
  FilterableDropdownComponent,
@@ -902,4 +903,16 @@ export class BulkEditorComponent
      )
    })
  }
+
+  emailSelected() {
+    const allHaveArchiveVersion = this.list.documents
+      .filter((d) => this.list.selected.has(d.id))
+      .every((doc) => !!doc.archived_file_name)
+
+    const modal = this.modalService.open(EmailDocumentDialogComponent, {
+      backdrop: 'static',
+    })
+    modal.componentInstance.documentIds = Array.from(this.list.selected)
+    modal.componentInstance.hasArchiveVersion = allHaveArchiveVersion
+  }
 }
--- a/src-ui/src/app/services/rest/document.service.spec.ts
+++ b/src-ui/src/app/services/rest/document.service.spec.ts
@@ -357,17 +357,15 @@ it('should include custom fields in sort fields if user has permission', () => {

 it('should call appropriate api endpoint for email document', () => {
  subscription = service
-    .emailDocument(
-      documents[0].id,
+    .emailDocuments(
+      [documents[0].id],
      'hello@paperless-ngx.com',
      'hello',
      'world',
      true
    )
    .subscribe()
-  httpTestingController.expectOne(
-    `${environment.apiBaseUrl}${endpoint}/${documents[0].id}/email/`
-  )
+  httpTestingController.expectOne(`${environment.apiBaseUrl}${endpoint}/email/`)
 })

 afterEach(() => {
--- a/src-ui/src/app/services/rest/document.service.ts
+++ b/src-ui/src/app/services/rest/document.service.ts
@@ -256,14 +256,15 @@ export class DocumentService extends AbstractPaperlessService<Document> {
    return this._searchQuery
  }

-  emailDocument(
-    documentId: number,
+  emailDocuments(
+    documentIds: number[],
    addresses: string,
    subject: string,
    message: string,
    useArchiveVersion: boolean
  ): Observable<any> {
-    return this.http.post(this.getResourceUrl(documentId, 'email'), {
+    return this.http.post(this.getResourceUrl(null, 'email'), {
+      documents: documentIds,
      addresses: addresses,
      subject: subject,
      message: message,
--- a/src/documents/mail.py
+++ b/src/documents/mail.py
@@ -10,11 +10,20 @@ def send_email(
    subject: str,
    body: str,
    to: list[str],
-    attachment: Path | None = None,
-    attachment_mime_type: str | None = None,
+    attachments: list[tuple[Path, str]],
 ) -> int:
    """
-    Send an email with an optional attachment.
+    Send an email with attachments.
+
+    Args:
+        subject: Email subject
+        body: Email body text
+        to: List of recipient email addresses
+        attachments: List of (path, mime_type) tuples for attachments (the list may be empty)
+
+    Returns:
+        Number of emails sent
+
    TODO: re-evaluate this pending https://code.djangoproject.com/ticket/35581 / https://github.com/django/django/pull/18966
    """
    email = EmailMessage(
@@ -22,17 +31,20 @@ def send_email(
        body=body,
        to=to,
    )
-    if attachment:
-        # Something could be renaming the file concurrently so it can't be attached
-        with FileLock(settings.MEDIA_LOCK), attachment.open("rb") as f:
-            content = f.read()
-            if attachment_mime_type == "message/rfc822":
-                # See https://forum.djangoproject.com/t/using-emailmessage-with-an-attached-email-file-crashes-due-to-non-ascii/37981
-                content = message_from_bytes(f.read())

-            email.attach(
-                filename=attachment.name,
-                content=content,
-                mimetype=attachment_mime_type,
-            )
+    # Something could be renaming the file concurrently so it can't be attached
+    with FileLock(settings.MEDIA_LOCK):
+        for attachment_path, mime_type in attachments:
+            with attachment_path.open("rb") as f:
+                content = f.read()
+                if mime_type == "message/rfc822":
+                    # See https://forum.djangoproject.com/t/using-emailmessage-with-an-attached-email-file-crashes-due-to-non-ascii/37981
+                    content = message_from_bytes(content)
+
+                email.attach(
+                    filename=attachment_path.name,
+                    content=content,
+                    mimetype=mime_type,
+                )
+
    return email.send()
--- a/src/documents/serialisers.py
+++ b/src/documents/serialisers.py
@@ -16,6 +16,7 @@ from django.contrib.auth.models import User
 from django.contrib.contenttypes.models import ContentType
 from django.core.exceptions import ValidationError
 from django.core.validators import DecimalValidator
+from django.core.validators import EmailValidator
 from django.core.validators import MaxLengthValidator
 from django.core.validators import RegexValidator
 from django.core.validators import integer_validator
@@ -1906,6 +1907,51 @@ class BulkDownloadSerializer(DocumentListSerializer):
        }[compression]


+class EmailSerializer(DocumentListSerializer):
+    addresses = serializers.CharField(
+        required=True,
+        label="Email addresses",
+        help_text="Comma-separated email addresses",
+    )
+
+    subject = serializers.CharField(
+        required=True,
+        label="Email subject",
+    )
+
+    message = serializers.CharField(
+        required=True,
+        label="Email message",
+    )
+
+    use_archive_version = serializers.BooleanField(
+        default=True,
+        label="Use archive version",
+        help_text="Use archive version of documents if available",
+    )
+
+    def validate_addresses(self, addresses):
+        address_list = [addr.strip() for addr in addresses.split(",")]
+        if not address_list:
+            raise serializers.ValidationError("At least one email address is required")
+
+        email_validator = EmailValidator()
+        try:
+            for address in address_list:
+                email_validator(address)
+        except ValidationError:
+            raise serializers.ValidationError(f"Invalid email address: {address}")
+
+        return ",".join(address_list)
+
+    def validate_documents(self, documents):
+        super().validate_documents(documents)
+        if not documents:
+            raise serializers.ValidationError("At least one document is required")
+
+        return documents
+
+
 class StoragePathSerializer(MatchingModelSerializer, OwnedObjectSerializer):
    class Meta:
        model = StoragePath
--- a/src/documents/signals/handlers.py
+++ b/src/documents/signals/handlers.py
@@ -1162,12 +1162,14 @@ def run_workflows(
            else ""
        )
        try:
+            attachments = []
+            if action.email.include_document and original_file:
+                attachments = [(original_file, document.mime_type)]
            n_messages = send_email(
                subject=subject,
                body=body,
                to=action.email.to.split(","),
-                attachment=original_file if action.email.include_document else None,
-                attachment_mime_type=document.mime_type,
+                attachments=attachments,
            )
            logger.debug(
                f"Sent {n_messages} notification email(s) to {action.email.to}",
--- a/src/documents/tests/test_api_documents.py
+++ b/src/documents/tests/test_api_documents.py
@@ -3093,7 +3093,7 @@ class TestDocumentApi(DirectoriesMixin, DocumentConsumeDelayMixin, APITestCase):
                "message": "hello",
            },
        )
-        self.assertEqual(resp.status_code, status.HTTP_404_NOT_FOUND)
+        self.assertEqual(resp.status_code, status.HTTP_400_BAD_REQUEST)

        resp = self.client.post(
            f"/api/documents/{doc.pk}/email/",
--- a/src/documents/tests/test_api_email.py
+++ b/src/documents/tests/test_api_email.py
@@ -0,0 +1,330 @@
+import json
+import shutil
+from unittest import mock
+
+from django.contrib.auth.models import Permission
+from django.contrib.auth.models import User
+from django.core import mail
+from django.test import override_settings
+from rest_framework import status
+from rest_framework.test import APITestCase
+
+from documents.models import Document
+from documents.tests.utils import DirectoriesMixin
+from documents.tests.utils import SampleDirMixin
+
+
+class TestEmail(DirectoriesMixin, SampleDirMixin, APITestCase):
+    ENDPOINT = "/api/documents/email/"
+
+    def setUp(self):
+        super().setUp()
+
+        self.user = User.objects.create_superuser(username="temp_admin")
+        self.client.force_authenticate(user=self.user)
+
+        self.doc1 = Document.objects.create(
+            title="test1",
+            mime_type="application/pdf",
+            content="this is document 1",
+            checksum="1",
+            filename="test1.pdf",
+            archive_checksum="A1",
+            archive_filename="archive1.pdf",
+        )
+        self.doc2 = Document.objects.create(
+            title="test2",
+            mime_type="application/pdf",
+            content="this is document 2",
+            checksum="2",
+            filename="test2.pdf",
+        )
+
+        # Copy sample files to document paths
+        shutil.copy(self.SAMPLE_DIR / "simple.pdf", self.doc1.archive_path)
+        shutil.copy(self.SAMPLE_DIR / "simple.pdf", self.doc1.source_path)
+        shutil.copy(self.SAMPLE_DIR / "simple.pdf", self.doc2.source_path)
+
+    @override_settings(
+        EMAIL_ENABLED=True,
+        EMAIL_BACKEND="django.core.mail.backends.locmem.EmailBackend",
+    )
+    def test_email_success(self):
+        """
+        GIVEN:
+            - Multiple existing documents
+        WHEN:
+            - API request is made to bulk email documents
+        THEN:
+            - Email is sent with all documents attached
+        """
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk, self.doc2.pk],
+                    "addresses": "hello@paperless-ngx.com,test@example.com",
+                    "subject": "Bulk email test",
+                    "message": "Here are your documents",
+                },
+            ),
+            content_type="application/json",
+        )
+
+        self.assertEqual(response.status_code, status.HTTP_200_OK)
+        self.assertEqual(response.data["message"], "Email sent")
+        self.assertEqual(len(mail.outbox), 1)
+
+        email = mail.outbox[0]
+        self.assertEqual(email.to, ["hello@paperless-ngx.com", "test@example.com"])
+        self.assertEqual(email.subject, "Bulk email test")
+        self.assertEqual(email.body, "Here are your documents")
+        self.assertEqual(len(email.attachments), 2)
+
+        # Check attachment names (should default to archive version for doc1, original for doc2)
+        attachment_names = [att[0] for att in email.attachments]
+        self.assertIn("archive1.pdf", attachment_names)
+        self.assertIn("test2.pdf", attachment_names)
+
+    @override_settings(
+        EMAIL_ENABLED=True,
+        EMAIL_BACKEND="django.core.mail.backends.locmem.EmailBackend",
+    )
+    def test_email_use_original_version(self):
+        """
+        GIVEN:
+            - Documents with archive versions
+        WHEN:
+            - API request is made to bulk email with use_archive_version=False
+        THEN:
+            - Original files are attached instead of archive versions
+        """
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk],
+                    "addresses": "test@example.com",
+                    "subject": "Test",
+                    "message": "Test message",
+                    "use_archive_version": False,
+                },
+            ),
+            content_type="application/json",
+        )
+
+        self.assertEqual(response.status_code, status.HTTP_200_OK)
+        self.assertEqual(len(mail.outbox), 1)
+        self.assertEqual(mail.outbox[0].attachments[0][0], "test1.pdf")
+
+    def test_email_missing_required_fields(self):
+        """
+        GIVEN:
+            - Request with missing required fields
+        WHEN:
+            - API request is made to bulk email endpoint
+        THEN:
+            - Bad request response is returned
+        """
+        # Missing addresses
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk],
+                    "subject": "Test",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+
+        # Missing subject
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk],
+                    "addresses": "test@example.com",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+
+        # Missing message
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk],
+                    "addresses": "test@example.com",
+                    "subject": "Test",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+
+        # Missing documents
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "addresses": "test@example.com",
+                    "subject": "Test",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+
+    def test_email_empty_document_list(self):
+        """
+        GIVEN:
+            - Request with empty document list
+        WHEN:
+            - API request is made to bulk email endpoint
+        THEN:
+            - Bad request response is returned
+        """
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [],
+                    "addresses": "test@example.com",
+                    "subject": "Test",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+
+    def test_email_invalid_document_id(self):
+        """
+        GIVEN:
+            - Request with non-existent document ID
+        WHEN:
+            - API request is made to bulk email endpoint
+        THEN:
+            - Bad request response is returned
+        """
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [999],
+                    "addresses": "test@example.com",
+                    "subject": "Test",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+
+    def test_email_invalid_email_address(self):
+        """
+        GIVEN:
+            - Request with invalid email address
+        WHEN:
+            - API request is made to bulk email endpoint
+        THEN:
+            - Bad request response is returned
+        """
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk],
+                    "addresses": "invalid-email",
+                    "subject": "Test",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+
+        # Test multiple addresses with one invalid
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk],
+                    "addresses": "valid@example.com,invalid-email",
+                    "subject": "Test",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+
+    def test_email_insufficient_permissions(self):
+        """
+        GIVEN:
+            - User without permissions to view document
+        WHEN:
+            - API request is made to bulk email documents
+        THEN:
+            - Forbidden response is returned
+        """
+        user1 = User.objects.create_user(username="test1")
+        user1.user_permissions.add(*Permission.objects.filter(codename="view_document"))
+
+        doc_owned = Document.objects.create(
+            title="owned_doc",
+            mime_type="application/pdf",
+            checksum="owned",
+            owner=self.user,
+        )
+
+        self.client.force_authenticate(user1)
+
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk, doc_owned.pk],
+                    "addresses": "test@example.com",
+                    "subject": "Test",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_403_FORBIDDEN)
+
+    @mock.patch(
+        "django.core.mail.message.EmailMessage.send",
+        side_effect=Exception("Email error"),
+    )
+    def test_email_send_error(self, mocked_send):
+        """
+        GIVEN:
+            - Existing documents
+        WHEN:
+            - API request is made to bulk email and error occurs during email send
+        THEN:
+            - Server error response is returned
+        """
+        response = self.client.post(
+            self.ENDPOINT,
+            json.dumps(
+                {
+                    "documents": [self.doc1.pk],
+                    "addresses": "test@example.com",
+                    "subject": "Test",
+                    "message": "Test message",
+                },
+            ),
+            content_type="application/json",
+        )
+        self.assertEqual(response.status_code, status.HTTP_500_INTERNAL_SERVER_ERROR)
+        self.assertIn("Error emailing documents", response.content.decode())
--- a/src/documents/views.py
+++ b/src/documents/views.py
@@ -57,6 +57,7 @@ from django_filters.rest_framework import DjangoFilterBackend
 from drf_spectacular.types import OpenApiTypes
 from drf_spectacular.utils import OpenApiParameter
 from drf_spectacular.utils import extend_schema
+from drf_spectacular.utils import extend_schema_serializer
 from drf_spectacular.utils import extend_schema_view
 from drf_spectacular.utils import inline_serializer
 from guardian.utils import get_group_obj_perms_model
@@ -153,6 +154,7 @@ from documents.serialisers import CustomFieldSerializer
 from documents.serialisers import DocumentListSerializer
 from documents.serialisers import DocumentSerializer
 from documents.serialisers import DocumentTypeSerializer
+from documents.serialisers import EmailSerializer
 from documents.serialisers import NotesSerializer
 from documents.serialisers import PostDocumentSerializer
 from documents.serialisers import RunTaskViewSerializer
@@ -471,6 +473,14 @@ class DocumentTypeViewSet(ModelViewSet, PermissionsAwareDocumentCountMixin):
    ordering_fields = ("name", "matching_algorithm", "match", "document_count")


+@extend_schema_serializer(
+    component_name="EmailDocumentRequest",
+    exclude_fields=("documents",),
+)
+class EmailDocumentDetailSchema(EmailSerializer):
+    pass
+
+
@extend_schema_view(
    retrieve=extend_schema(
        description="Retrieve a single document",
@@ -638,20 +648,28 @@ class DocumentTypeViewSet(ModelViewSet, PermissionsAwareDocumentCountMixin):
            404: None,
        },
    ),
-    email=extend_schema(
+    email_document=extend_schema(
        description="Email the document to one or more recipients as an attachment.",
-        request=inline_serializer(
-            name="EmailRequest",
-            fields={
-                "addresses": serializers.CharField(),
-                "subject": serializers.CharField(),
-                "message": serializers.CharField(),
-                "use_archive_version": serializers.BooleanField(default=True),
-            },
-        ),
+        request=EmailDocumentDetailSchema,
        responses={
            200: inline_serializer(
-                name="EmailResponse",
+                name="EmailDocumentResponse",
+                fields={"message": serializers.CharField()},
+            ),
+            400: None,
+            403: None,
+            404: None,
+            500: None,
+        },
+        deprecated=True,
+    ),
+    email_documents=extend_schema(
+        operation_id="email_documents",
+        description="Email one or more documents as attachments to one or more recipients.",
+        request=EmailSerializer,
+        responses={
+            200: inline_serializer(
+                name="EmailDocumentsResponse",
                fields={"message": serializers.CharField()},
            ),
            400: None,
@@ -1155,55 +1173,65 @@ class DocumentViewSet(

        return Response(sorted(entries, key=lambda x: x["timestamp"], reverse=True))

-    @action(methods=["post"], detail=True)
-    def email(self, request, pk=None):
-        try:
-            doc = Document.objects.select_related("owner").get(pk=pk)
+    @action(methods=["post"], detail=True, url_path="email")
+    # TODO: deprecated as of 2.19, remove in future release
+    def email_document(self, request, pk=None):
+        request_data = request.data.copy()
+        request_data.setlist("documents", [pk])
+        return self.email_documents(request, data=request_data)
+
+    @action(
+        methods=["post"],
+        detail=False,
+        url_path="email",
+        serializer_class=EmailSerializer,
+    )
+    def email_documents(self, request, data=None):
+        serializer = EmailSerializer(data=data or request.data)
+        serializer.is_valid(raise_exception=True)
+
+        validated_data = serializer.validated_data
+        document_ids = validated_data.get("documents")
+        addresses = validated_data.get("addresses").split(",")
+        addresses = [addr.strip() for addr in addresses]
+        subject = validated_data.get("subject")
+        message = validated_data.get("message")
+        use_archive_version = validated_data.get("use_archive_version", True)
+
+        documents = Document.objects.select_related("owner").filter(pk__in=document_ids)
+        for document in documents:
            if request.user is not None and not has_perms_owner_aware(
                request.user,
                "view_document",
-                doc,
+                document,
            ):
                return HttpResponseForbidden("Insufficient permissions")
-        except Document.DoesNotExist:
-            raise Http404
+
+        attachments = []
+        for doc in documents:
+            attachment_path = (
+                doc.archive_path
+                if use_archive_version and doc.has_archive_version
+                else doc.source_path
+            )
+            attachments.append((attachment_path, doc.mime_type))

        try:
-            if (
-                "addresses" not in request.data
-                or "subject" not in request.data
-                or "message" not in request.data
-            ):
-                return HttpResponseBadRequest("Missing required fields")
-
-            use_archive_version = request.data.get("use_archive_version", True)
-
-            addresses = request.data.get("addresses").split(",")
-            if not all(
-                re.match(r"[^@]+@[^@]+\.[^@]+", address.strip())
-                for address in addresses
-            ):
-                return HttpResponseBadRequest("Invalid email address found")
-
            send_email(
-                subject=request.data.get("subject"),
-                body=request.data.get("message"),
+                subject=subject,
+                body=message,
                to=addresses,
-                attachment=(
-                    doc.archive_path
-                    if use_archive_version and doc.has_archive_version
-                    else doc.source_path
-                ),
-                attachment_mime_type=doc.mime_type,
+                attachments=attachments,
            )
+
            logger.debug(
-                f"Sent document {doc.id} via email to {addresses}",
+                f"Sent documents {[doc.id for doc in documents]} via email to {addresses}",
            )
            return Response({"message": "Email sent"})
        except Exception as e:
-            logger.warning(f"An error occurred emailing document: {e!s}")
+            logger.warning(f"An error occurred emailing documents: {e!s}")
            return HttpResponseServerError(
-                "Error emailing document, check logs for more detail.",
+                "Error emailing documents, check logs for more detail.",
            )


--- a/uv.lock
+++ b/uv.lock
@@ -1036,11 +1036,11 @@ wheels = [

 [[package]]
 name = "filelock"
-version = "3.19.1"
+version = "3.20.0"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/40/bb/0ab3e58d22305b6f5440629d20683af28959bf793d98d11950e305c1c326/filelock-3.19.1.tar.gz", hash = "sha256:66eda1888b0171c998b35be2bcc0f6d75c388a7ce20c3f3f37aa8e96c2dddf58", size = 17687, upload-time = "2025-08-14T16:56:03.016Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/58/46/0028a82567109b5ef6e4d2a1f04a583fb513e6cf9527fcdd09afd817deeb/filelock-3.20.0.tar.gz", hash = "sha256:711e943b4ec6be42e1d4e6690b48dc175c822967466bb31c0c293f34334c13f4", size = 18922, upload-time = "2025-10-08T18:03:50.056Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/42/14/42b2651a2f46b022ccd948bca9f2d5af0fd8929c4eec235b8d6d844fbe67/filelock-3.19.1-py3-none-any.whl", hash = "sha256:d38e30481def20772f5baf097c122c3babc4fcdb7e14e57049eb9d88c6dc017d", size = 15988, upload-time = "2025-08-14T16:56:01.633Z" },
+    { url = "https://files.pythonhosted.org/packages/76/91/7216b27286936c16f5b4d0c530087e4a54eead683e6b0b73dd0c64844af6/filelock-3.20.0-py3-none-any.whl", hash = "sha256:339b4732ffda5cd79b13f4e2711a31b0365ce445d95d243bb996273d072546a2", size = 16054, upload-time = "2025-10-08T18:03:48.35Z" },
 ]

 [[package]]
@@ -1795,12 +1795,11 @@ wheels = [

 [[package]]
 name = "mkdocs-material"
-version = "9.6.20"
+version = "9.6.21"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
    { name = "babel", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
    { name = "backrefs", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
-    { name = "click", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
    { name = "colorama", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
    { name = "jinja2", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
    { name = "markdown", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
@@ -1811,9 +1810,9 @@ dependencies = [
    { name = "pymdown-extensions", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
    { name = "requests", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/ba/ee/6ed7fc739bd7591485c8bec67d5984508d3f2733e708f32714c21593341a/mkdocs_material-9.6.20.tar.gz", hash = "sha256:e1f84d21ec5fb730673c4259b2e0d39f8d32a3fef613e3a8e7094b012d43e790", size = 4037822, upload-time = "2025-09-15T08:48:01.816Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/ff/d5/ab83ca9aa314954b0a9e8849780bdd01866a3cfcb15ffb7e3a61ca06ff0b/mkdocs_material-9.6.21.tar.gz", hash = "sha256:b01aa6d2731322438056f360f0e623d3faae981f8f2d8c68b1b973f4f2657870", size = 4043097, upload-time = "2025-09-30T19:11:27.517Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/67/d8/a31dd52e657bf12b20574706d07df8d767e1ab4340f9bfb9ce73950e5e59/mkdocs_material-9.6.20-py3-none-any.whl", hash = "sha256:b8d8c8b0444c7c06dd984b55ba456ce731f0035c5a1533cc86793618eb1e6c82", size = 9193367, upload-time = "2025-09-15T08:47:58.722Z" },
+    { url = "https://files.pythonhosted.org/packages/cf/4f/98681c2030375fe9b057dbfb9008b68f46c07dddf583f4df09bf8075e37f/mkdocs_material-9.6.21-py3-none-any.whl", hash = "sha256:aa6a5ab6fb4f6d381588ac51da8782a4d3757cb3d1b174f81a2ec126e1f22c92", size = 9203097, upload-time = "2025-09-30T19:11:24.063Z" },
 ]

 [[package]]
@@ -1922,7 +1921,7 @@ sdist = { url = "https://files.pythonhosted.org/packages/61/68/810093cb579daae42

 [[package]]
 name = "nltk"
-version = "3.9.1"
+version = "3.9.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
    { name = "click", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
@@ -1930,9 +1929,9 @@ dependencies = [
    { name = "regex", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
    { name = "tqdm", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/3c/87/db8be88ad32c2d042420b6fd9ffd4a149f9a0d7f0e86b3f543be2eeeedd2/nltk-3.9.1.tar.gz", hash = "sha256:87d127bd3de4bd89a4f81265e5fa59cb1b199b27440175370f7417d2bc7ae868", size = 2904691, upload-time = "2024-08-18T19:48:37.769Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/f9/76/3a5e4312c19a028770f86fd7c058cf9f4ec4321c6cf7526bab998a5b683c/nltk-3.9.2.tar.gz", hash = "sha256:0f409e9b069ca4177c1903c3e843eef90c7e92992fa4931ae607da6de49e1419", size = 2887629, upload-time = "2025-10-01T07:19:23.764Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/4d/66/7d9e26593edda06e8cb531874633f7c2372279c3b0f46235539fe546df8b/nltk-3.9.1-py3-none-any.whl", hash = "sha256:4fa26829c5b00715afe3061398a8989dc643b92ce7dd93fb4585a70930d168a1", size = 1505442, upload-time = "2024-08-18T19:48:21.909Z" },
+    { url = "https://files.pythonhosted.org/packages/60/90/81ac364ef94209c100e12579629dc92bf7a709a84af32f8c551b02c07e94/nltk-3.9.2-py3-none-any.whl", hash = "sha256:1e209d2b3009110635ed9709a67a1a3e33a10f799490fa71cf4bec218c11c88a", size = 1513404, upload-time = "2025-10-01T07:19:21.648Z" },
 ]

 [[package]]
@@ -2280,7 +2279,7 @@ requires-dist = [
    { name = "drf-spectacular", specifier = "~=0.28" },
    { name = "drf-spectacular-sidecar", specifier = "~=2025.9.1" },
    { name = "drf-writable-nested", specifier = "~=0.7.1" },
-    { name = "filelock", specifier = "~=3.19.1" },
+    { name = "filelock", specifier = "~=3.20.0" },
    { name = "flower", specifier = "~=2.0.1" },
    { name = "gotenberg-client", specifier = "~=0.11.0" },
    { name = "granian", extras = ["uvloop"], marker = "extra == 'webserver'", specifier = "~=2.5.1" },
@@ -2328,7 +2327,7 @@ dev = [
    { name = "mkdocs-glightbox", specifier = "~=0.5.1" },
    { name = "mkdocs-material", specifier = "~=9.6.4" },
    { name = "pre-commit", specifier = "~=4.3.0" },
-    { name = "pre-commit-uv", specifier = "~=4.1.3" },
+    { name = "pre-commit-uv", specifier = "~=4.2.0" },
    { name = "pytest", specifier = "~=8.4.1" },
    { name = "pytest-cov", specifier = "~=7.0.0" },
    { name = "pytest-django", specifier = "~=4.11.1" },
@@ -2338,7 +2337,7 @@ dev = [
    { name = "pytest-rerunfailures" },
    { name = "pytest-sugar" },
    { name = "pytest-xdist" },
-    { name = "ruff", specifier = "~=0.13.0" },
+    { name = "ruff", specifier = "~=0.14.0" },
 ]
 docs = [
    { name = "mkdocs-glightbox", specifier = "~=0.5.1" },
@@ -2346,8 +2345,8 @@ docs = [
 ]
 lint = [
    { name = "pre-commit", specifier = "~=4.3.0" },
-    { name = "pre-commit-uv", specifier = "~=4.1.3" },
-    { name = "ruff", specifier = "~=0.13.0" },
+    { name = "pre-commit-uv", specifier = "~=4.2.0" },
+    { name = "ruff", specifier = "~=0.14.0" },
 ]
 testing = [
    { name = "daphne" },
@@ -2642,15 +2641,15 @@ wheels = [

 [[package]]
 name = "pre-commit-uv"
-version = "4.1.5"
+version = "4.2.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
    { name = "pre-commit", marker = "sys_platform == 'darwin' or sys_platform == 'linux'" },
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