How to send unsupported file type attachments or oversize files via emails using base64



Most company email exchanges have file size limits and block sending or receiving zip files, media files or other 'unknown' file types within or outside the company network.  You may not necessarily realize any restrictions until you feel like a fool when you emailed your clients without the expected attachments.   Some companies may create file sharing with public endpoints allowing you to upload, download and share with your clients outside the company network.  However, this also assumes your recipients do not have the similar policies for uploading or downloading files outside their network given zip or unknown file types are always red-flagged.   Some may suggest changing the file extension to .txt or other known file extensions.  Does it work?  Sometimes but don't bet on it.   Even it may work the first couple times but will eventually get caught, it's just a matter of time.  Base64 encoding any file type to text is your best bet.  It increases the file size ~25% but it works for any file type and you may break them into multiple text files to meet the file size limitation your company may impose.   I used to have to communicate with clients outside my company network so I certainly felt the pain.  A simple solution to encode and decode base64 is CLI but definitely not fast while business teams keep complaining and asking us to develop a tool for them.  Internal tools always get de-prioritized among feature requests so it goes nowhere.  

Recently, I got a chance to try an offline desktop tool "OEDcoder" which is exactly what we need.  It is much less expensive than allocating resources for a team to build one and the performance is insanely fast with bulk processing which CLI lacks.  In addition, business analysts and product managers need to review site snapshots daily but what they can get from our databases are all base64 encoded.  Some of the business and product team members think it is 'cool' to use CLI (feel more 'techie') but most of them hate it especially during promotions or site outages who keep pinging us as P0 to decode for them ASAP.  These additional yet unnecessary encoding/decoding support can be completely eliminated with a $6 offline tool.   Depending on your company, some can expense any tools less than $100 without prior approval while other may need to go through your license acquisition team even for a 99 cents single licensing approval.  

Read my other post if you want to learn more about the performance of this lightweight offline tool "OEDcoder" and why I recommend it.     


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