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Can't Send email: "Executable File Violation"

  • 07-06-2017 3:59pm
    #1
    Mark Hamill
    Registered Users, Registered Users 2 Posts: 7,792 ✭✭✭


    99% of the emails I send from my work email get to their destinations fine, but a small handful of customers claim to not receive them. They maintain that we have some setting on our end that prevents them getting through their firewalls. Of those emails, I have only had 1 or two bounce back with an actually error response, namely an email from "IT@yourcompany.com" with the text:
    You attempted to send a message that contained an executable file. Our company policy prohibits the sending of executable files via email. The message was not delivered.
    I do not send executable files via email, only jpgs (scanned pages) and pdfs.

    Could there be an error on my end, or is it more likely that their mail server is in the wrong?


Comments

  • #2
    jimgoose
    Registered Users, Registered Users 2 Posts: 20,195 ✭✭✭✭jimgoose


    Are you sure you're not sending the odd macro-enabled Excel or Word doc as an attachment? I know Symantec Messaging Gateway, for one, picks up most of those as executable.


  • #3
    Mark Hamill
    Registered Users, Registered Users 2 Posts: 7,792 ✭✭✭Mark Hamill


    jimgoose wrote: »
    Are you sure you're not sending the odd macro-enabled Excel or Word doc as an attachment? I know Symantec Messaging Gateway, for one, picks up most of those as executable.

    No, I'm sure it's just pdfs and jpegs.


  • #4
    TallGlass
    Closed Accounts Posts: 4,935 ✭✭✭TallGlass


    Mark Hamill wrote: »
    No, I'm sure it's just pdfs and jpegs.

    That could be a generic mail bounce back from there server for all extensions blocked/file size to large.

    How big are the emails?

    My suggestion. Try zipping the docs up and compress them down then send.


  • #5
    Mark Hamill
    Registered Users, Registered Users 2 Posts: 7,792 ✭✭✭Mark Hamill


    TallGlass wrote: »
    That could be a generic mail bounce back from there server for all extensions blocked/file size to large.

    How big are the emails?

    My suggestion. Try zipping the docs up and compress them down then send.

    Jpgs are <400kb, pdfs <100kb.
    Thing is, emails with the same attachments don't fail if they are coming from our gmail account.
    I'll try compressing the next time I have to send to an email I know will fail otherwise.


  • #6
    jimgoose
    Registered Users, Registered Users 2 Posts: 20,195 ✭✭✭✭jimgoose


    Mark Hamill wrote: »
    Jpgs are <400kb, pdfs <100kb.
    Thing is, emails with the same attachments don't fail if they are coming from our gmail account.
    I'll try compressing the next time I have to send to an email I know will fail otherwise.

    Hmm. Sometimes happens that a particular mail client will MIME-encode compressed or PDF files as "application/x-compressed" and get flagged as executable by Symantec's rule. The newer True Type Executable Files rule works a lot better in these situations.


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  • #7
    TallGlass
    Closed Accounts Posts: 4,935 ✭✭✭TallGlass


    Mark Hamill wrote: »
    Jpgs are <400kb, pdfs <100kb.
    Thing is, emails with the same attachments don't fail if they are coming from our gmail account.
    I'll try compressing the next time I have to send to an email I know will fail otherwise.

    Do non attachment emails get to this server? If not, could there be something in the footers added by the server tripping the end server.

    As jimgoose mentions, sounds like some bad rules or some rules need updating on there end.


  • #8
    ED E
    Registered Users, Registered Users 2 Posts: 36,170 ✭✭✭✭ED E


    TallGlass wrote: »
    Do non attachment emails get to this server? If not, could there be something in the footers added by the server tripping the end server.

    This is where you need to look.


  • #9
    Mark Hamill
    Registered Users, Registered Users 2 Posts: 7,792 ✭✭✭Mark Hamill


    jimgoose wrote: »
    Hmm. Sometimes happens that a particular mail client will MIME-encode compressed or PDF files as "application/x-compressed" and get flagged as executable by Symantec's rule. The newer True Type Executable Files rule works a lot better in these situations.
    TallGlass wrote: »
    Do non attachment emails get to this server? If not, could there be something in the footers added by the server tripping the end server.

    As jimgoose mentions, sounds like some bad rules or some rules need updating on there end.

    I would have to check (nearly everything we send out has attachments) but I think that might be the case. If so, is that something that is fixed on my end, or on their end?


  • #10
    jimgoose
    Registered Users, Registered Users 2 Posts: 20,195 ✭✭✭✭jimgoose


    Mark Hamill wrote: »
    I would have to check (nearly everything we send out has attachments) but I think that might be the case. If so, is that something that is fixed on my end, or on their end?

    The mail server end, I should say. That is, their end.


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