Opening " Forbidden Files" in Outlook

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SUMMARY

The forum discussion centers on the challenges of opening a "suspect" file in Outlook, specifically a zip file containing an executable (.exe) extension. Users express concerns about potential malware, emphasizing that Outlook does not allow access to the file due to security settings. The conversation highlights the limitations of antivirus software in scanning nested zip files and suggests that creating multiple layers of zip files can bypass antivirus restrictions. Ultimately, participants recommend caution and suggest deleting the file if there are any doubts about its safety.

PREREQUISITES
  • Understanding of Outlook security settings and file attachment protocols
  • Familiarity with zip file formats and executable file extensions
  • Knowledge of antivirus software functionality and limitations
  • Basic understanding of Python's tkinter library and its applications
NEXT STEPS
  • Research methods to configure Outlook to allow access to suspect files
  • Learn about antivirus software capabilities in scanning nested zip files
  • Explore safe practices for handling executable files received via email
  • Investigate alternative file-sharing methods that enhance security
USEFUL FOR

This discussion is beneficial for IT professionals, cybersecurity experts, and anyone involved in email communication and file sharing who needs to understand the risks associated with opening suspect files in Outlook.

WWGD
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TL;DR
Received a " Forbidden " file I know comes from trustworthy source in Outlook. How do I open it?
Hi all,
I received an attached file marked as " suspect" in Outlook, i.e., with the circle with diagonal red slash. I know who sent it to me; they were in front of me at the coffee shop and I know the person. Outlook is not giving me the option, AFAIK, to open it, nor even to inspect it. Any ideas on how to open it?
Thanks.
 
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Why would you want to open a suspect file? Did you intercept the transmission of this file?

it could well have a malware component. I’d delete and forget it.
 
jedishrfu said:
Why would you want to open a suspect file? Did you intercept the transmission of this file?

it could well have a malware component. I’d delete and forget it.
No, someone I know sent it to me. Right in front of me, at Sbux.
 
And you ran a virus checker on the other person's computer before they sent it, right?
 
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It's a zip file with an exe extension. It should be fine.
 
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Vanadium 50 said:
And you ran a virus checker on the other person's computer before they sent it, right?
It's hard to tell since I remember the message that Windows does not consider Outlook, one of its programs, a trusted source. So evidence is all over the place. But I agree a false positive is better and being cautious/Conservative. I was told by the sender, in person, the content ( please see my reply to Russ below) But I agree it's best to just let go.
 
I c
russ_watters said:
It's a zip file with an exe extension. It should be fine.
I can't even gauge what the extension is by pointing the cursor towards it. I can't access the file's properties , thus it's extension. I know it contains code from Python's tkinter library.
 
It's not unusual for antivirus checking programs to block code as they don't know what it is. Antivirus programs can and do check inside zip files for harmful content. There is usually a limit though as to how "deep" into the zip file they can go to check stuff, in my experience it is usually 2 zip files deep.

In my experience if you create a zip file, then create a 2nd zip file containing the 1st zip file, then create a 3rd zip file containing the 2nd zip file...this will usually be enough for the antivirus program not to be able to scan it and allow it through.
 
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