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Html_file = codecs.open(html_doc, 'r', 'utf-8', errors='ignore') #Opens HTML file and converts to UTF-8, ignoring errors Html_doc = os.path.join((os.environ),sig_html_path) #Specifies the name of the HTML version of the stored signature Signature_path = os.path.join((os.environ), sig_files_path) # Finds the path to Outlook signature files with signature name "Work"

Sig_html_path = 'AppData\Roaming\Microsoft\Signatures\\' + signature_name + '.htm' sig_files_path = 'AppData\Roaming\Microsoft\Signatures\\' + signature_name + '_files\\' It seems I needed to replace the local path to the Signature files, with the absolute path in order to use images,etc.

NewMail.HTMLBody = "Email Message" + signature_code NewMail.BodyFormat = 2 # olFormatHTML (v=office.11).aspx Signature_code = signature_code.replace('Work_files/', signature_path) #Replaces local directory with full directory path Signature_code = html_file.read() #Writes contents of HTML signature file to a string Html_file = codecs.open(html_doc, 'r', 'utf-8', errors='ignore') #Opens HTML file and ignores errors Html_doc = html_doc.replace('\\\\', '\\') #Removes escape backslashes from path string Html_doc = os.path.join((os.environ),'AppData\Roaming\Microsoft\Signatures\Work.htm') #Specifies the name of the HTML version of the stored signature Signature_path = os.path.join((os.environ),'AppData\Roaming\Microsoft\Signatures\Work_files\\') # Finds the path to Outlook signature files with signature name "Work" You can find the signature in Outlook stored as an HTML file in %APPDATA%\Microsoft\Signatures and I used the following code to copy the file contents and add them to my email body import win32com.client If you want to programmatically insert a signature, Redemption (I am its author) exposes RDOSignature object which implements ApplyTo method (it handles the signature image files and merges HTML styles appropriately). Now Only MailItem.Display adds the signature to an unmodified message. UPDATE: as of the latest (Summer 2016) builds of Outlook, GetInspector trick no longer works. Mail.HTMLBody now contains the message signature that you will need to merger (not just concatenate!) with your own HTML Outlook = win32.Dispatch('outlook.application') Note that Outlook adds a signature when an unmodified message is displayed or its inspector is touched import win32com.client as win32 You would also need to merge the styles from two HTML documents and take care of the embedded images used by the signature. Keep in mind that two HTML strings must be merged, not just concatenated. The best you can do is read the signature from the file system and add its contents to the HTML body appropriately. Outlook signatures are not exposed through the Outlook Object Model.