diff --git a/apps/remix/app/components/dialogs/template-use-dialog-document-name.tsx b/apps/remix/app/components/dialogs/template-use-dialog-document-name.tsx
new file mode 100644
index 000000000..4e12cc392
--- /dev/null
+++ b/apps/remix/app/components/dialogs/template-use-dialog-document-name.tsx
@@ -0,0 +1,201 @@
+import { DOCUMENT_TITLE_MAX_LENGTH } from '@documenso/trpc/server/document-router/schema';
+import { cn } from '@documenso/ui/lib/utils';
+import { FormControl, FormField, FormItem, FormLabel, FormMessage } from '@documenso/ui/primitives/form/form';
+import { Input } from '@documenso/ui/primitives/input';
+import { RadioGroup, RadioGroupItem } from '@documenso/ui/primitives/radio-group';
+import { msg } from '@lingui/core/macro';
+import { Trans, useLingui } from '@lingui/react/macro';
+import { useEffect } from 'react';
+import { useFormContext, useWatch } from 'react-hook-form';
+import { z } from 'zod';
+
+export const DOCUMENT_NAME_SOURCE = {
+  TEMPLATE: 'template',
+  UPLOAD: 'upload',
+  CUSTOM: 'custom',
+} as const;
+
+type TDocumentNameSource = (typeof DOCUMENT_NAME_SOURCE)[keyof typeof DOCUMENT_NAME_SOURCE];
+
+type TTemplateUseCustomDocumentData = {
+  data?: File;
+};
+
+type TTemplateUseDocumentNameData = {
+  documentNameSource: TDocumentNameSource;
+  customDocumentName: string;
+  customDocumentData?: TTemplateUseCustomDocumentData[];
+};
+
+type TTemplateUseDocumentNameFormValues = TTemplateUseDocumentNameData & {
+  useCustomDocument: boolean;
+};
+
+const getUploadedDocumentTitle = (customDocumentData?: TTemplateUseCustomDocumentData[]) => {
+  const uploadedFiles = customDocumentData?.map((item) => item.data).filter((file): file is File => file !== undefined);
+
+  if (uploadedFiles?.length !== 1) {
+    return undefined;
+  }
+
+  return uploadedFiles[0].name.replace(/\.[^/.]+$/, '').trim();
+};
+
+export const getTemplateUseDocumentTitle = (data: TTemplateUseDocumentNameData) => {
+  switch (data.documentNameSource) {
+    case DOCUMENT_NAME_SOURCE.TEMPLATE:
+      return undefined;
+    case DOCUMENT_NAME_SOURCE.UPLOAD:
+      return getUploadedDocumentTitle(data.customDocumentData);
+    case DOCUMENT_NAME_SOURCE.CUSTOM:
+      return data.customDocumentName.trim();
+    default: {
+      const exhaustiveCheck: never = data.documentNameSource;
+
+      return exhaustiveCheck;
+    }
+  }
+};
+
+export const refineTemplateUseDocumentName = (data: TTemplateUseDocumentNameData, ctx: z.RefinementCtx) => {
+  if (data.documentNameSource === DOCUMENT_NAME_SOURCE.TEMPLATE) {
+    return;
+  }
+
+  const title = getTemplateUseDocumentTitle(data);
+  const path = data.documentNameSource === DOCUMENT_NAME_SOURCE.CUSTOM ? 'customDocumentName' : 'documentNameSource';
+
+  if (!title) {
+    ctx.addIssue({
+      code: z.ZodIssueCode.custom,
+      message:
+        data.documentNameSource === DOCUMENT_NAME_SOURCE.CUSTOM
+          ? msg`Document name is required`.id
+          : msg`Select exactly one uploaded document to use its file name.`.id,
+      path: [path],
+    });
+
+    return;
+  }
+
+  if (title.length > DOCUMENT_TITLE_MAX_LENGTH) {
+    ctx.addIssue({
+      code: z.ZodIssueCode.custom,
+      message: msg`Document name is too long`.id,
+      path: [path],
+    });
+  }
+};
+
+export const TemplateUseDialogDocumentName = () => {
+  const { t } = useLingui();
+  const { clearErrors, control, setValue } = useFormContext<TTemplateUseDocumentNameFormValues>();
+  const [useCustomDocument, documentNameSource, customDocumentData] = useWatch({
+    control,
+    name: ['useCustomDocument', 'documentNameSource', 'customDocumentData'],
+  });
+
+  const uploadedDocumentCount = customDocumentData?.filter((item) => item.data !== undefined).length ?? 0;
+  const canUseUploadedDocumentName = useCustomDocument && uploadedDocumentCount === 1;
+
+  useEffect(() => {
+    if (documentNameSource !== DOCUMENT_NAME_SOURCE.UPLOAD || canUseUploadedDocumentName) {
+      return;
+    }
+
+    setValue('documentNameSource', DOCUMENT_NAME_SOURCE.TEMPLATE);
+    clearErrors('documentNameSource');
+  }, [canUseUploadedDocumentName, clearErrors, documentNameSource, setValue]);
+
+  return (
+    <>
+      <FormField
+        control={control}
+        name="documentNameSource"
+        render={({ field }) => (
+          <FormItem>
+            <FormLabel>
+              <Trans>Document name</Trans>
+            </FormLabel>
+            <FormControl>
+              <RadioGroup
+                aria-label={t`Document name`}
+                value={field.value}
+                onValueChange={(value) => {
+                  field.onChange(value);
+
+                  if (value !== DOCUMENT_NAME_SOURCE.CUSTOM) {
+                    clearErrors('customDocumentName');
+                  }
+
+                  if (value !== DOCUMENT_NAME_SOURCE.UPLOAD) {
+                    clearErrors('documentNameSource');
+                  }
+                }}
+                className="space-y-2"
+              >
+                <div className="flex items-center gap-2">
+                  <RadioGroupItem id="document-name-source-template" value={DOCUMENT_NAME_SOURCE.TEMPLATE} />
+                  <label className="text-sm" htmlFor="document-name-source-template">
+                    <Trans>Use template name</Trans>
+                  </label>
+                </div>
+
+                <div className="flex items-start gap-2">
+                  <RadioGroupItem
+                    id="document-name-source-upload"
+                    value={DOCUMENT_NAME_SOURCE.UPLOAD}
+                    disabled={!canUseUploadedDocumentName}
+                    className="mt-0.5"
+                  />
+                  <div>
+                    <label
+                      className={cn('text-sm', {
+                        'cursor-not-allowed text-muted-foreground': !canUseUploadedDocumentName,
+                      })}
+                      htmlFor="document-name-source-upload"
+                    >
+                      <Trans>Use uploaded file name</Trans>
+                    </label>
+
+                    {!canUseUploadedDocumentName && (
+                      <p className="text-muted-foreground text-xs">
+                        <Trans>Select exactly one uploaded document to use its file name.</Trans>
+                      </p>
+                    )}
+                  </div>
+                </div>
+
+                <div className="flex items-center gap-2">
+                  <RadioGroupItem id="document-name-source-custom" value={DOCUMENT_NAME_SOURCE.CUSTOM} />
+                  <label className="text-sm" htmlFor="document-name-source-custom">
+                    <Trans>Enter custom document name</Trans>
+                  </label>
+                </div>
+              </RadioGroup>
+            </FormControl>
+            <FormMessage />
+          </FormItem>
+        )}
+      />
+
+      {documentNameSource === DOCUMENT_NAME_SOURCE.CUSTOM && (
+        <FormField
+          control={control}
+          name="customDocumentName"
+          render={({ field }) => (
+            <FormItem className="ml-6">
+              <FormLabel>
+                <Trans>Custom document name</Trans>
+              </FormLabel>
+              <FormControl>
+                <Input {...field} placeholder={t`Enter a document name`} />
+              </FormControl>
+              <FormMessage />
+            </FormItem>
+          )}
+        />
+      )}
+    </>
+  );
+};
diff --git a/apps/remix/app/components/dialogs/template-use-dialog.tsx b/apps/remix/app/components/dialogs/template-use-dialog.tsx
index 48507fb7d..84d438819 100644
--- a/apps/remix/app/components/dialogs/template-use-dialog.tsx
+++ b/apps/remix/app/components/dialogs/template-use-dialog.tsx
@@ -38,27 +38,44 @@ import { useNavigate } from 'react-router';
 import * as z from 'zod';
 import { getTemplateUseErrorMessage } from '~/utils/toast-error-messages';
 
-const ZAddRecipientsForNewDocumentSchema = z.object({
-  distributeDocument: z.boolean(),
-  useCustomDocument: z.boolean().default(false),
-  customDocumentData: z
-    .array(
+import {
+  DOCUMENT_NAME_SOURCE,
+  getTemplateUseDocumentTitle,
+  refineTemplateUseDocumentName,
+  TemplateUseDialogDocumentName,
+} from './template-use-dialog-document-name';
+
+const ZAddRecipientsForNewDocumentSchema = z
+  .object({
+    distributeDocument: z.boolean(),
+    useCustomDocument: z.boolean().default(false),
+    documentNameSource: z.enum([
+      DOCUMENT_NAME_SOURCE.TEMPLATE,
+      DOCUMENT_NAME_SOURCE.UPLOAD,
+      DOCUMENT_NAME_SOURCE.CUSTOM,
+    ]),
+    customDocumentName: z.string(),
+    customDocumentData: z
+      .array(
+        z.object({
+          title: z.string(),
+          data: z.instanceof(File).optional(),
+          envelopeItemId: z.string(),
+        }),
+      )
+      .optional(),
+    recipients: z.array(
       z.object({
-        title: z.string(),
-        data: z.instanceof(File).optional(),
-        envelopeItemId: z.string(),
+        id: z.number(),
+        email: ZRecipientEmailSchema,
+        name: z.string(),
+        signingOrder: z.number().optional(),
       }),
-    )
-    .optional(),
-  recipients: z.array(
-    z.object({
-      id: z.number(),
-      email: ZRecipientEmailSchema,
-      name: z.string(),
-      signingOrder: z.number().optional(),
-    }),
-  ),
-});
+    ),
+  })
+  .superRefine((data, ctx) => {
+    refineTemplateUseDocumentName(data, ctx);
+  });
 
 type TAddRecipientsForNewDocumentSchema = z.infer<typeof ZAddRecipientsForNewDocumentSchema>;
 
@@ -106,6 +123,8 @@ export function TemplateUseDialog({
     return {
       distributeDocument: false,
       useCustomDocument: false,
+      documentNameSource: DOCUMENT_NAME_SOURCE.TEMPLATE,
+      customDocumentName: '',
       customDocumentData: envelopeItems.map((item) => ({
         title: item.title,
         data: undefined,
@@ -142,6 +161,8 @@ export function TemplateUseDialog({
 
   const onSubmit = async (data: TAddRecipientsForNewDocumentSchema) => {
     try {
+      const documentTitle = getTemplateUseDocumentTitle(data);
+
       const customFilesToUpload = (data.customDocumentData || []).filter(
         (item): item is { data: File; envelopeItemId: string; title: string } =>
           item.data !== undefined && item.envelopeItemId !== undefined && item.title !== undefined,
@@ -163,6 +184,7 @@ export function TemplateUseDialog({
         recipients: data.recipients,
         distributeDocument: data.distributeDocument,
         customDocumentData,
+        ...(documentTitle ? { override: { title: documentTitle } } : {}),
       });
 
       toast({
@@ -195,6 +217,8 @@ export function TemplateUseDialog({
     name: 'recipients',
   });
 
+  const useCustomDocument = form.watch('useCustomDocument');
+
   useEffect(() => {
     if (open) {
       form.reset(generateDefaultFormValues());
@@ -401,7 +425,16 @@ export function TemplateUseDialog({
                           onCheckedChange={(checked) => {
                             field.onChange(checked);
                             if (!checked) {
-                              form.setValue('customDocumentData', undefined);
+                              const customDocumentData = form.getValues('customDocumentData');
+
+                              form.setValue(
+                                'customDocumentData',
+                                customDocumentData?.map((item) => ({
+                                  ...item,
+                                  data: undefined,
+                                })),
+                              );
+                              form.clearErrors('customDocumentData');
                             }
                           }}
                         />
@@ -428,7 +461,7 @@ export function TemplateUseDialog({
                   )}
                 />
 
-                {form.watch('useCustomDocument') && (
+                {useCustomDocument && (
                   <div className="my-4 space-y-2">
                     {isLoadingEnvelopeItems ? (
                       <SpinnerBox className="py-16" />
@@ -537,6 +570,7 @@ export function TemplateUseDialog({
                                         }
 
                                         field.onChange(file);
+                                        form.clearErrors('customDocumentData');
                                       }}
                                     />
                                   </div>
@@ -550,6 +584,8 @@ export function TemplateUseDialog({
                     )}
                   </div>
                 )}
+
+                <TemplateUseDialogDocumentName />
               </div>
 
               <DialogFooter className="mt-4">