Set Up and Send Secure Documents

Updated November 20, 2025 01:32

How to create templates, upload documents, and send important files to families using Secure Document Delivery. This step-by-step guide covers template setup, document processing, and job management for report cards, progress reports, and other student documents.

Who can use this?
School and District Admins and those with the individual user permission for Manage Secure Documents.

Before getting started

Secure Document Delivery must be enabled for your district (primarily a district-level feature).
Admins can contact ParentSquare support to enable Secure Document Delivery.
You need a sample PDF document with student IDs to create your first template.

Click Play or watch on Vimeo.

Create a Template

Before sending documents to families, you must create a template that defines where to find student IDs in your documents. You can use a single student's document to create your template. The template tells the system how to split a large PDF file with student-specific information for multiple students into individual documents for each family.

From Add-Ons, select Secure Documents in the left sidebar and click New Template.
Enter a Template Title and upload a Sample PDF. The sample PDF should be a full page that clearly identifies where to find the student ID. For PDF specifications, see PDF Requirements.
Select Student ID Type: Choose either SIS ID or State ID based on which identifier appears in your documents.
A preview of the sample PDF will be displayed. Click and drag to draw a rectangle around the position where the student ID is located. This includes any invisible Student ID. Make the box large enough to pick up the Student ID on any page in case the positioning varies from page to page.
Click Save Selection to confirm the student ID location on this template.
Optional: To help find the Student ID, add a regular expression (sequence that defines the search pattern) to Student ID pattern. Click Test to check that the expected Student ID is found. For comprehensive regex guidance, see the Troubleshooting article.

Tip: Make the bounding box larger rather than smaller. If the system cannot find student IDs consistently, widen the box or adjust the regular expression pattern.

Send Documents from Your Template

From Add-Ons, select Secure Documents in the left sidebar and click Send from Template for the desired template.
Upload a multiple-page PDF file and enter the Total Number of Documents. The total number of documents should match the total number of students in the uploaded file. The system will split each document by student ID, even for documents with varying page counts. For PDF specifications, see PDF Requirements.
If the number of documents found does not match what you entered, you will receive a warning message. Review the following options.
- Click Don't Send: Fix the documents and try uploading again. This is recommended if there is a significant mismatch.
- Type OK then Send Anyway: Proceed only if you are certain the count is correct despite the warning.
  
  Note: For Educational Rights Holder, see Educational Rights Holder (ERH) Restrictions for the remaining steps.
After processing finishes, you'll see the number of documents created. The system will flag any documents where it couldn't find a student ID.
Click View next to a student's name to preview the document that will be sent to their family and confirm that the pages were split correctly.
Review the list for any students marked as "Not Found." These students either do not exist in ParentSquare or their ID does not match the ID in your uploaded file.
Type the subject and body of the notification to send with the documents. Keep the message clear and concise. Parents will receive this message via their preferred notification methods (email, text, or app notification).
Review your notification text for clarity. Include information about what the document contains and any actions parents should take.
You have two options for delivering documents to families:
- Send Immediately: Click Send to deliver documents right away. Parents will receive notifications within minutes based on their delivery preferences.
- Schedule for Later: Click the dropdown arrow next to Send and select Schedule. Choose a specific date and time for delivery. This is useful for sending documents during business hours or coordinating with other communications.

Important Note: Always preview at least a few documents before sending to verify that the template is working correctly and pages are split as expected.

PDF Requirements

Before using Secure Documents, verify that your documents meet these technical requirements:

PDF format: Document must be an editable (vector) PDF, not scanned images or rasterized files. PDF/X format is recommended for best results.
Student ID placement: Student IDs must appear on the first page of each document in a consistent location. Student IDs must be horizontal across the page. Note: You cannot use Staff IDs to send a document.
PDF length: Each student's document must be at least one full page (cannot split a single page between students). Documents should not be rotated. The system may not detect student IDs correctly if orientation is incorrect.
Font requirements: All fonts must be embedded in the PDF file.

Manage Templates and Jobs

All sent, scheduled, and draft documents are organized in the Jobs section. You can view status, edit scheduled deliveries, or delete drafts as needed.

From the Templates tab:

From Add-ons, select Secure Documents in the left sidebar, then click the Templates tab.
Locate your template and click the number above Jobs to see all associated jobs for that specific template. Note: When a template is deleted from the Templates tab, all associated jobs will also be removed. Delete templates carefully to avoid losing scheduled or draft jobs.

From the Jobs tab:

From Add-ons, select Secure Documents in the left sidebar, then click the Jobs tab.
Locate a job by status (All, Draft, Scheduled, or Sent) or select a specific Template from the dropdown menu to narrow the results.
Scheduled: For any scheduled job, you can modify it before it sends:
- Delete: Removes the job. The template remains in your Template list.
- Cancel Schedule: Returns the job to "Draft" status so you can edit or reschedule.
- Send/Schedule: Send immediately, edit the notification message, or change the scheduled date and time.
Draft: You can send or delete drafts at any time:
- Delete: Removes the job. The template remains in your Template list.
- Send/Schedule: Send immediately, edit the notification message, or choose when it will be sent.

Email Confirmation for Scheduled Jobs

When you schedule a job, you will receive an email confirmation. The email includes:

Subject line: "Your documents are ready for: [title]"
Sent from: donotreply@parentsquare.com
A link to view and manage the scheduled job

Educational Rights Holder (ERH) Restrictions

Some districts are required by state law to limit access to certain student documents—such as state assessment results or other confidential records—to parents or guardians who hold educational rights (often referred to as custodial parents). The Educational Rights Holder (ERH) setting allows districts to meet these requirements by sending secure documents only to parents marked as ERH.

When ERH restrictions are enabled at the district level, ParentSquare automatically checks each student’s ERH status during upload and sending. Administrators receive clear indicators showing which students have at least one ERH-designated parent, helping them understand who can receive documents and which families may require follow-up by mail.

Note: When the ERH feature is enabled, all Secure Documents—whether sent by the district or an individual school—are delivered only to parents with the ERH indicator. There is no option to send Secure Documents to non-ERH contacts while this setting is active.

Configure ERH Data

Before enabling Secure Document Delivery with ERH restrictions, ensure that your student information system is providing ERH data to ParentSquare. See help articles for data administrators.

ERH data can currently be delivered through SFTP or Aeries.
Confirm that the educational_rights field is included in the parents.csv file that is regularly sent to your district’s SFTP folder.
If ERH data is missing or incomplete, documents may not be deliverable for some students.

Send Secure Documents with ERH Enabled

Sending documents with ERH restrictions follows the same basic process as standard Secure Document Delivery, with a few extra checks:

Follow steps 1-3 of Send Documents from Your Template to upload your PDF and generate documents.
After the documents are generated, review the Educational Rights Holder column to see which students have at least one eligible parent.
Note: If you do not see this column, contact your district admin.
Before sending, verify the number of students who are able to receive the document based on ERH status.
Click Send.
ParentSquare will perform an ERH Check indicating:
- How many students have an ERH and will receive a document.
- How many students do not have an ERH and therefore cannot receive it.
If some students cannot be sent their document, type OK and Send Anyway to proceed or click Don't Send to review.
After sending, open the Secure Document Delivery Report to view delivery status and confirm with families received their document. See Secure Document Delivery Reports.

Handling Undeliverable Documents

For students who do not have a parent marked as ERH, their document will not be delivered digitally. These documents can be downloaded from the delivery report and mailed or distributed using traditional methods. See Mail Undelivered Documents in Secure Document Delivery Reports.