ChartCaddy supports digital signatures for users, digitized signatures for clients, and sending for electronic signatures via a third party.

When a single user needs to sign a document, first they get the document to Completed status. At that point a field to enter their password and a "Sign" button appear, and to digitally sign a document the user enters the same password they used to log into the system into the field and clicks the Sign button. This creates a digital fingerprint of the data so that it can be determined later if anything has changed since the user signed it. Once a document is signed by a user then it can not be changed. An administrator can take the document back to Draft, but in that case what really happens is the original document is flagged as deleted and a copy of the original is presented as the new Draft document. If a chart item has been revised, the previous revision can be viewed by clicking the History button on the chart item, and then by clicking Prev Revision. Documents flagged as deleted can be listed and viewed by searching for them with the Chart Items report. Multiple chart items may be signed at once using the Chart Items report.

To sign a document the client is presented with blank space on the document and the client uses a stylus or their finger to sign their name. The signature is displayed on the document after the client signs it. By default client digitized signatures are disabled, and can only be enabled by requesting that a document be customized to add it.

Instead of a single user clicking the Sign button to digitally sign a document they can click the "Send For Sigs" buttons, which initiates a process for multiple people to digitally sign the document in a secure and HIPAA compliant manner. This method is disabled by default because it is an additional cost. Both Chart Items and Templates can be digitally signed via the Send For Signatures process. Recipient can either receive a link via email to sign the document or they sign it immediately from ChartCaddy. Once the user clicks Send For Sigs the status of the document changes from Completed to Provisional and a recipient verification screen is shown. Possible recipients consist of users listed on the document, any supervisors of users listed on the document, the client listed on the document, and any people associated with the client. People like relatives, guardians, and contacts can be associated with a client on the Client Information screen. When as user clicks the Send For Sigs button a verification screen is presented for two reasons. The main reason is so that the user can verify that everybody that needs to sign the document is listed, has a valid and unique email, and is marked as being required to sign the document. If any people or email addresses are missing the user can resolve that issue elsewhere in the system and then click Send For Sigs button on the document again to resume the process where they left off. The other main reason for the verification screen is to exclude any people associated with the client that should not sign the document.

Once the user verifies that the recipient information is correct they can either click the "Sign Now" or "Send" button to initiate the process. The Send button is only available initially, immediately sends an email to the first recipient, and once a recipient signs the document an email is automatically sent to the next recipient. The Sign Now button immediately loads the document to be signed by the next recipient. Until all the people listed have signed the document the process can be canceled by clicking the "Cancel" button, the next recipient can sign immediately by clicking the "Sign Now" button,  or an email reminder can be sent to the next recipient by clicking the "Send Reminder" button.

Once all the people have signed the document a digitally signed PDF of the document is automatically downloaded and attached to the original document in ChartCaddy, and the status of the document in the system changes to Signed.

Templates can be attached to both client Charts and Contacts (incoming referrals) and are signed using the Send For Sigs process. Currently available templates are: