How do I get a document signed on Outlook using Secure Exchanges?

Sign a document in Microsoft Outlook using Secure Exchanges

This article explains how to send a PDF document for signature with Secure Exchanges directly from Microsoft Outlook, from creating the email to defining the signature areas.

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Prerequisites

Before you begin, make sure you have:

  • The Secure Exchanges plug-in for Outlook is installed.
  • The plug-in for defining signature areas in PDF documents

1. Create the email and add the signatories

  1. In Outlook, click on "New email" and compose your message as usual.
  2. Next, add the signatories of the document in the "To" field.
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The signing process is done in a chain : each signatory receives the document in turn, in the order of the addresses entered.
People added to CC will receive a copy of the signed document, but will not sign it. If you want people in BCC and BCC to be signatories, here is the procedure to follow:

2. Add the document and send the email

  1. Using the "Signature" button in the Outlook ribbon, in the Secure Exchanges section, insert the PDF document to be signed.

  1. When your message is ready, click "Send".
  2. The Secure Exchanges window opens automatically.

In this window, you can:
  1. Indicate whether you need to sign the document . *In this case, check the box "I need to sign the documents".
  2. define signature areas
  3. adjust the document's behavior before sending

3. Configure the signature in Secure Exchanges

Notes
In the signature area definition interface, various options are accessible at the top of the screen to adjust the document's behavior. The sections below explain each of these options in detail.
"Sign and send" option


The "Sign and send" option allows you to sign a document yourself and send it immediately to a third party, in a single step.

This option is particularly useful when you need to, for example, sign a contract and send it directly to a client or partner.

When you select this option, you will be prompted to sign the document directly within the signature area definition interface. Once the signature is complete, simply enter the recipient's email address in the "To" field.

The recipient will then receive the final signed copy of the document, and you will have only sent one email for the entire process.
Option "Use digital signature certificates"


When the "Use digital signature certificates" option is checked, the document is signed using digital signature certificates recognized by Adobe.

In practical terms, this means that:
  1. Each signature affixed to the document is cryptographically linked to the content of the PDF.
  2. The document includes complete traceability: identity of signatories, timestamps, and signature history.
  3. The document remains valid over time (long-term validation – LTV), even if the certificates expire or if the document is accessed offline.
  4. Any modification after signing automatically invalidates the document, which is clearly indicated in Adobe Acrobat or Adobe Reader.
From a technical point of view, the document retains its integrity:
  1. The digital signature is generated from a cryptographic hash (SHA-512) of the document, without altering its content.
What this changes in the PDF document:
  1. When this option is enabled, signature fields are integrated as true fillable PDF fields, and not as simple visual annotations.
  2. You will have new fields such as:
    1. Text area (multiline)

    2. Drop-down list (with predefined choices and multiple selection option)


    3. List of options (multiple selections)


  3. In Adobe Acrobat or Adobe Reader, the document will clearly display that the signature is valid, with:
  1. the certified identity of the signatory
  2. the exact date and time of the signature
  3. validation history



Option "Do not add Secure Exchange signing certificates to the document"


 By default, when you don't use digital signature certificates, Secure Exchanges automatically adds its validation certificates to the end of the signed document. However, some organizations reject documents when additional pages are automatically added to the end of the file. When you select this option, no signature certificate pages are added to the PDF document after signing.
Notes
Even if these pages are not added:
  1. the document remains valid
  2. Signatures can always be verified and validated.
  3. Validation can be performed using the Secure Exchanges document validator.

Option "Do not lock the document after signing"


The "Do not lock the document after signing" option allows you to disable this behavior, but should be used with caution.
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We recommend that you use the "Use digital signature certificates" option.

4. Define the signature areas

Using your cursor, draw the areas to be completed directly on the PDF document.

For each zone, you can choose the desired field type:

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Certain fields are only available when using digital signature certificates.
  1. signature or initials
  1. text (single or multi-line)
  1. date or calendar
  1. number
  1. checkbox
  1. radio button
  1. drop-down list
  1. list of options (multiple selections)
If the document has multiple signatories, select each signatory from the dropdown list and define their areas, one at a time for each of them.


Once all fields have been defined for all signers, click "Apply" in the upper left corner. You can then configure the sending settings and click "Send with Secure Exchanges".



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