Resource Sending delayed / scheduled messages / goodbye notes, etc

[jgm63]

SUMMARY / TLDR

> Write your "goodbye note", etc, in an MS Word document, and password-protect to encrypt the document.
> Use gmail to compose an email. Schedule it to send later using gmail's built-in auto-scheduling.
Attach the encrypted MS Word document to the mail. In the message body, write something like : "Please read attached document. Password to open document will be sent in separate email - check spam/junk folder if not received".
> Use a different email auto scheduling service, eg "later.io", to send the password, with a message, eg : "Here is the password to open the document sent to you in the other email : <put password here> Check spam/junk folder if other email not received". Schedule that to send around the same time as the first mail discussed above.
> The steps above prevent gmail monitoring from spotting any trigger/danger keywords, since those would only be inside the encrypted document, which gmail can't access. We don't use gmail to send the password, to ensure gmail staff can't open the document.
> There's various subtle points you should get right, so it's worth reading the full guide.


FULL GUIDE

> Write your "goodbye note", or other messages etc, in an MS Word document, and password-protect the document.
The protected document will almost certainly be encrypted (unless you're on a very old MS-Word version). You'll probably see an option "encrypt with password" (or similar), which should confirm encryption is being used.

> Use gmail to compose an email. We won't send this mail now, but schedule it to send later using gmail's built-in auto-scheduling.
Attach the encrypted MS Word document to the mail. In the message body, write something like : "Please read attached document. Password to open document will be sent in separate email - check spam/junk folder if not received".
On the gmail "send" button is a little down arrow. Click that arrow, click "Schedule send", and select the future date and time.

NOTE : Don't trust gmail built-in scheduling for sensitive messages, since those messages would be stored on gmail servers and may be monitored for keywords, etc. Attaching an encrypted document should be okay, however, since the document contents are only accessible by knowing the password. Don't put anything suspicious in visible parts of the email, eg don't write "Attached document below is my goodbye note" etc.

> Use another *different* email auto scheduling service, such as "later.io" or "mailbutler", to send the password, with a message, eg : "Here is the password to open the document sent to you in the other email : <put password here> Check spam/junk folder if other email not received".
Schedule that email to send around the same time as the first mail discussed above (perhaps a few minutes later).
I haven't researched later.io or mailbutler in-depth. If you know of other good server-based email scheduling services, then please post info below. LetterMeLater signup appears to now redirect to later.io. I did a quick test of later.io and it worked fine.
NOTE : If you were to send this email from gmail, then gmail staff could access the information from both emails, and open the encrypted document, so this is why a different service must be used.

Further notes :
> Don't use a document name that could raise suspicion, eg "ending_it_all.docx" is *not* a good filename - gmail staff may be concerned. In general future scheduled emails might be more closely monitored than immediate-send emails.

> Use a strong password
I believe the MS Word password length is limited to 15 characters.
I suggest using that maximum length.
Use a random mix of upper/lower case, numbers. I've avoided symbols in case it confuses the recipient.
example : dAvdRY3JVH26dcs ( example only, don't actually use that )
If the intended recipient is not very computer literate then you could just use lower-case letters plus numbers, but still try to use 15 characters. Stick to random sequences of characters and avoid known words, etc.
You could generate the password using https://passwordsgenerator.net/ (Set length to 15. Tick "numbers" / "lowercase" / "uppercase" / "generate on your device", untick the other boxes)

> Test the process in advance (obviously using different destination email addresses to the final intended recipients)
When testing, power off your computer to ensure the email scheduling services don't need your computer be be on.

> Avoid scheduled email services such as outlook that require your computer to be powered on.

> If you make a CTB attempt that fails, or you decide not to CTB, etc, then you'll want to cancel at least one of the scheduled emails, preferably both. NOTE : IT COULD BE EASY TO FORGET THIS, SO PERHAPS WRITE YOURSELF A "CANCEL EMAILS !!!" NOTE THAT YOU'LL SEE IF THIS HAPPENS.
In gmail there's a "scheduled" folder. If you "tick" the scheduled mail, a "cancel send" button appears, which will move the mail into the draft folder.
You should test you can do this from your mobile, since you may not have access to your computer if this happens.
In later.io or mailbutler, etc, it should be straightforward to figure out how to cancel (I haven't checked the exact steps).

> You could use a 2 stage process :
The stage 1 document could just say (eg) : "I'm sorry for what has happened. Another auto-scheduled email will arrive in one month's time with an explanation of everything". The stage 1 emails could be scheduled for 2 or 3 days after your attempt.
The stage 2 document can contain the full note / explanation, etc, and can be scheduled for one month later.
The idea is that if you were incapacitated after an attempt, you have up to one month to cancel the second stage emails that provide the full explanation. For each "stage", you would set up two emails, as explained above, so in total there will be 4 scheduled emails (you're basically repeating the whole process twice).


Other options

If you have an android phone, there's an app "Do It Later", that supports delayed SMS / gmail messages.
I believe the SMS part works (I haven't tried it personally). I don't know about the gmail part.
I believe it offers good privacy. I believe the messages are only stored locally on your phone until they are sent.
(A good way to verify the app privacy would be to schedule an SMS/email, power off your phone, and confirm no messages are sent while your phone is off. This would give additional confidence that the messages are only being stored on your phone, and not on any server where they could be seen by others. I haven't done such a test yet, but if anyone tests this to verify, then please post below).
If using this app, there shouldn't be any need for encrypting or attaching documents, etc.
You can simply write whatever you need to, and schedule it for sending.
Your phone would need to have enough battery power to last until the messages are sent. You may want to leave it on charge / plugged in.
Also, the SMS part would need a network signal, and the gmail part would need the internet connection (wifi or network signal).
Obviously you should do some tests, ideally with your phone "locked", to see if your test messages get sent.
However, the "double email" method discussed above is probably better, since it doesn't rely on your phone or computer having power and a signal.
More info :

Spoiler: future-text-question

https://sanctioned-suicide.net/threads/future-text-question.27657/

Spoiler: doitlater website

HOME

www.doitlater.co

An alternative to the main method explained in the guide above, where 2 delayed emails are used, is to send one email now, and send the other as the delayed/scheduled email.
e.g. send encrypted document now, send password in delayed mail. If doing this, ensure the password is not guessable. Or you could send the password now, and send the encrypted document in the delayed mail.
These approaches aren't recommended, since they may cause premature worry when the first email arrives.
The minor advantage is there's slightly less to go wrong, since you're only relying on one scheduled email service, however the original method of two delayed emails should be okay, assuming reliable service providers are used.
NOTE : You should still send the emails from different service providers, eg the first mail could be sent from any email service (eg outlook etc), and the delayed email could be sent from gmail. If you sent both mails from gmail, then gmail could open the encrypted document (gmail can access the future mail as soon as you schedule it, since it's stored on their servers).

 

[jgm63]

[ bump, various changes made, should be a lot easier to follow now ]

 

[TAW122]

This is a good read, and bookmarked. Also just wondering, even though MS Word's document is password encrypted, is it possible for Google's AI to pick up the contents of the word document by any chance? (Might be a dumb question, but it is an important factor.) Aside from this, I think this is a good idea.

 

[jgm63]

This is a good read, and bookmarked. Also just wondering, even though MS Word's document is password encrypted, is it possible for Google's AI to pick up the contents of the word document by any chance? (Might be a dumb question, but it is an important factor.) Aside from this, I think this is a good idea.

MS Word uses fairly good encryption. The exact encryption strength depends on the version of word used.
Provided you use a strong password, it should be almost impossible, for anyone who doesn't know the password, to access the document.
If you use a random mix of 15 upper/lower case and numbers for your password, then there are 26 * 2 + 10 possibilities for each character = 62. This translates to 62 to the power of 15 (the password length) possible passwords, which is 7.7E26 (about a billion billion billion).
Trying each password will involve thousands or millions of CPU instruction executions.
It will therefore be "computationally infeasible" to try to crack the document using "brute force" in this way, unless perhaps a very large supercomputer were used, which is a very scarce resource.
However, if you use a weak password, then all bets are off....
So you should follow the password recommendations given in the guide.
There is, however, another aspect to consider, and that is whether the encryption algorithm used has any "backdoor" engineered into it.
This is a topic of much conspiracy-theory-ism, and I can't advise whether the encryption used by MS Word might have a "backdoor".
If it had a backdoor it would be "big news" and would likely become well known very quickly, unless only some select "inner circle" know the backdoor, which is possible. To the best of my knowledge, it should be safe to use the guide above, provided the strong password caveats are applied.
However, things are always changing, so we never know how long what is safe today will remain safe, so it's wise to be cautious...

 

[jgm63]

This is a good read, and bookmarked. Also just wondering, even though MS Word's document is password encrypted, is it possible for Google's AI to pick up the contents of the word document by any chance? (Might be a dumb question, but it is an important factor.) Aside from this, I think this is a good idea.

PS.....
To further clarify, above I wrote "Trying each password will involve thousands or millions of CPU instruction executions."

What I mean is that to try even *one* password out would likely need hundreds of thousands or millions of instructions to be executed, and that there are about 7.7E26 (about a billion billion billion) possible passwords (if you follow the strong password recommendations given).
When you multiply those two factors together, it makes "brute force" trying of all possible passwords infeasible, so there is no way to "crack" the password.

So I consider it to be safe, and that nobody would be able to access the document *provided* you follow the strong password recommendations given in the guide....

 

[Jean4]

NOTES ON TESTING THE PROCESS :

To avoid emails being sent to spam/junk folders, try to ensure the recipient has your email addresses saved in their contacts/address book.

If possible, you would send the intended recipient(s) some test messages in advance, using the same auto-schedule methods you will be using when you schedule the actual emails, and check that they receive them.

The test emails should be virtually identical to the real emails that will be sent. So ideally you would attach a password-protected document, and also send the email containing the password, as part of the test. Obviously you would not put your actual goodbye note in the attached document - you would use some other document contents. You would use the same email service providers and method of scheduling the emails, etc. The only difference between the test emails and the actual emails to be sent should be the date/time and the contents of the attached document.

A possible cover story would be to put something the recipient might be interested in or need, etc, into the attached document, so there is a reason for sending it. If there were some reason for that information to be kept private, then that might justify the password protection and sending of password in a separate email. e.g. If there were information that would make sense for them to have a copy of for safe keeping / backup then that could be a viable story, etc. Or you could send them any information in the document that might interest them, and say that you wanted to test the password-protection, etc. If you have access to the intended recipient's computer (or email account), then you can ignore the "cover story" aspect if needed, assuming you can delete the mails after testing without the recipient noticing them. However, you should still avoid putting your actual goodbye note in the document, in case anything goes wrong with the test.

To make the test realistic, ideally make the "please open document" (etc) messages the same as the actual messages you intend to send later. The closer you make the test to the actual messages to be sent the better. This proves the messages get past spam filters. As stated, don't put your actual goodbye note in the test version of the attached document - use other document contents, but ideally of a similar length (in case the spam filter depends in some way on document length). Obviously if you haven't written your goodbye note yet then the "similar length" condition may be difficult to achieve, although you could take a best guess (or wait until you've written your note, and then do these tests).

If you have access to the intended recipient's computer (or email account), then you could do the test mentioned, check the two emails arrive in their inbox and don't go to spam, and check you can get the password from the password email, then open the password-protected attached document from the email containing it. You would then delete those emails from their inbox before they see them. You may also need to delete them from the "deleted" or "trash" (etc) folder, so they're permanently deleted. You could tweak the instructions you will write in your email explaining how to open the document, based on the exact steps you had to perform to open the document if they were non-obvious or if the recipient is not very tech-savvy. If you modify the email in that way, then in theory you should re-test, in case the spam filter reacts differently to your modified email text. If the emails went to spam/junk during the first or second test, then try adding your email addresses to their contacts/address book, and repeat the test. You might be able to add a rule to never send emails from your two addresses (one address for the document, one address for the password) to spam.

You could then repeat the test (assuming you have an adequate "cover story"), but this time wait for the recipient themselves to receive and open the document, to verify that they will notice receiving the email and can perform the action successfully themselves. You could include something like : "Test : Please call me and quote code <put a number or codeword here> to confirm you got this message" into the document, then wait to see if they call you.

If you don't have access to the intended recipient's computer, then you would only be doing the latter test where you wait for the recipient to receive and open the document.

As part of the test you would try to confirm that they received both emails, and were able to open the password-protected attached document, and read its contents. You would look for them to confirm what they read in the document. Doing these tests should indicate whether the messages will get past any spam filters.

If you had to explain to the recipient how to open the document then you may wish to include that explanation in the actual email you send later.
In theory, making that modification means you should test again, to ensure the new email still gets past the spam filter.

NOTE If your testing is done one recipient at a time, then it would be best to send your final emails in the same way, since something unexpected may occur if using multiple recipients at once (eg possible spam filter issue, etc). As stated, the aim is for the final email sending to be as similar as possible to the testing, except for the document contents. If you want your final emails to go to multiple recipients at once, then your test should use the same approach.

Missed you Cecil

 

[jgm63]

NOTES ON TESTING THE PROCESS (updated version)

The general idea is to send test messages to the intended recipient(s) in advance, using the same auto-schedule methods you'll be using when you schedule the actual emails, and check they receive and can access them.

Avoid emails going to spam/junk by ensuring recipient has your email addresses in their contacts/address book. Do this for both addresses (one for sending document, one for sending password). Alternatively, setup rules to not send mails from your addresses to spam.

General method
Send intended recipient(s) test messages using same auto-schedule methods you'll be using for actual emails.
Try to send test mails that are identical to the real mails you'll send later, except contents of attached document.
Use same service providers as you will use for actual mails.
Attach password-protected document in one mail and send another mail containing password (assuming that's the method you'll use for actual mails)
Obviously don't put the actual goodbye note in document, use some other contents (ideally of similar length).
If you decide to modify the mails in any way during testing then in theory you should retest, to confirm the mails get past the spam filter.

Test procedure
If you have access to intended recipient's computer or email account, then :
> Send test emails as explained above.
> Check the 2 emails arrive and don't go to spam.
> If they went to spam/junk then add your email addresses to their contacts/address book or add rule to not send emails from your addresses to spam. Then repeat test.
> Check you can get password from password email, then open password-protected attached document from the email containing it, and read contents.
> Delete those emails from inbox, then delete from "deleted" or "trash" (etc) folders, to leave no record.

If you have a "cover story" (see below) to explain why you're sending the mails, then :
> Send test emails as explained above.
> Confirm recipient(s) noticed the emails and could open document using password.
> Confirm some specific content from the document to prove they could read it.
> Check if they had to go to spam/junk to find the emails. If so, ask them to add your email addresses in their contacts/address book or setup a rule to not send emails from your addresses to spam. Then repeat test.

Note on multiple recipients : If your testing is done one recipient at a time, then you should send your final emails in the same way, since something unexpected may occur if using multiple recipients at once (eg possible spam filter issue, etc). The aim is for the final email sending to be as similar as possible to the testing, except for the contents inside the document. If you want your final emails to go to multiple recipients at once, then your test should use the same approach.


FURTHER INFO

"cover story" options to explain why you're sending the mails :
Put something the recipient might be interested in or need, etc, into the attached document, so there is a reason for sending it. If there were some reason for that information to be kept private, then that might justify the password protection and sending of password in a separate email. e.g. If there were information that would make sense for them to have a copy of for safe keeping / backup then that could be a viable story, etc. Or you could send them any information in the document that might interest them, and say that you wanted to test the password-protection, etc.

Ideally make the "please open document" (etc) message body text the same as the actual text you intend to send later. The closer you make the test to the actual messages to be sent, the better. This proves the messages get past spam filters.

As stated, don't put your actual goodbye note in the test version of the attached document - use other document contents, but ideally of a similar length (in case the spam filter depends in some way on document length). Obviously if you haven't written your goodbye note yet then the "similar length" condition may be difficult to achieve, although you could take a best guess, or do these tests after you've written your note.

If you have access to the intended recipient's computer or email account and you do the test explained above where you access their inbox, then you could tweak the instructions you will write in your email explaining how to open the document, based on the exact steps you had to perform if they were non-obvious or if the recipient is not very tech-savvy. If you modify the email in that way, then in theory you should re-test, in case the spam filter reacts differently to your modified email body text.

If you have a "cover story" and are getting the intended recipient(s) to open the test email/document, then you could include something like : "This is a test : Please call me and quote code <put a number or codeword here> to confirm you got this message" into the document, then wait to see if they call you.

If you had to explain to the recipient how to open the document then you may wish to include that explanation in the actual email you send later. In theory, you should test again, to ensure the new email still gets past the spam filter.

 

[ManWithNoName]

Good points made.

What about saving the message as a high res jpeg? Or place the jpeg in a PDF with password?

 

[Largeletters]

Thank you, this was very informative, and I will think about taking up some of these methods.

 

[davidlynchfan666]

I tested the Do It Late app by setting a qued email and shutting my phone, and it didn't send when my phone was off so I'm assuming that means that it's stored on the phone and not in a cloud? When I downloaded it, it also told me to make sure that my phone doesn't turn off the app as a power-saving measure, so that's more proof that the message doesn't need to be encrypted.

 

[Goaway]

The issue that I face is that when there is a delayed email, I am concerned that after I CTB someone could simply log into my account and either stop the send or read the emails as they would have access to the encrypted Word document and the email that contains the password. Has anyone thought about a solution to that issue ? Thanks.

 

[jgm63]

I tested the Do It Late app by setting a qued email and shutting my phone, and it didn't send when my phone was off so I'm assuming that means that it's stored on the phone and not in a cloud? When I downloaded it, it also told me to make sure that my phone doesn't turn off the app as a power-saving measure, so that's more proof that the message doesn't need to be encrypted.

Ok, so that seems to confirm what we know about "Do It Later".
So....
Pros :
Don't need to encrypt anything or attach documents, etc.

Cons :
Phone needs enough battery power to last until messages sent (maybe leave it on charge / plugged in)
SMS would need network signal, email would need internet connection (wifi or network signal)

Those "cons" are significant, however, so people will have to decide whether they're comfortable with the risk of a message not being sent.

 

[jgm63]

The issue that I face is that when there is a delayed email, I am concerned that after I CTB someone could simply log into my account and either stop the send or read the emails as they would have access to the encrypted Word document and the email that contains the password. Has anyone thought about a solution to that issue ? Thanks.

If you use strong passwords, that only you know, then you should be okay.....
A strong password should be a random mix of upper/lower case letters, numbers, symbols.
Aim for 16 (ideally 18) or more characters. Example : vpH783@dg!VN5968R1
If you're not using strong passwords currently, then change your passwords.

Just make sure you remember your own passwords, so you can cancel the emails if you need to.

You should :
Clear your browser history and cookies, etc.
Delete any saved passwords in your browser.
Verify that to get back into your email, it asks for your password.
Check there's no way to get in without knowing the password.

General handling of passwords :
One way of "remembering" (storing) your passwords is to have a password-protected (encrypted) MS Word document, where you keep a record of your passwords.
One "master" password, which you need to remember, opens the word document, and you can then access all your other passwords.
This allows you to use many different complex (strong) passwords, without having to remember them.
This is effectively a makeshift/manual version of a "password manager" (alternatively you could use an actual password manager).
Make sure you use a strong master password.
You would want to keep a backup of that document.
You may also want to write down some "hints" to help you remember your master password.

 

[ArtsyDrawer]

For a second there my heart skipped thinking about you leaving.
I'm a selfish fuck, I'm aware. I don't know how to not be a selfish fuck.
This is a very good piece, though, imo, for people who want to leave a note but not fuss about being found too soon.

 

[benjaminbusdriver]

Could a Dropbox link work instead? Would they also have a way to scan the doc and intervene, as you say Google could possibly do? It could be just one email on time delay with the private link to the PDF file. I'm coordinating my plan today and testing etc...

 

[jgm63]

Could a Dropbox link work instead? Would they also have a way to scan the doc and intervene, as you say Google could possibly do? It could be just one email on time delay with the private link to the PDF file. I'm coordinating my plan today and testing etc...

If the dropbox link were not publicly accessible, but were only accessible by the recipient (and perhaps a limited group of other people), then I think that would be okay, provided the company providing the scheduled email service is not the same company providing the file hosting.

If the dropbox link were publicly accessible, then it brings me back to considering that we don't really know what scanning tools they may or may not have. Also, could there be a possibility of manual checking for future scheduled emails ?
Personally I don't know if I would feel comfortable with "hoping" that those don't apply.
I would want something I *know* is fairly watertight.
The encrypted document scheme explained in the first post offers that.

There could be other approaches.....

You could "hide" a document somewhere on the recipients machine, and the delayed email could tell them where to find it. In that case you would want to ensure the document does not appear in any "recent" lists at the OS level, or within any applications.

You could place a document on a USB key, and the delayed email could tell them where to find it. Again, ensure the document does not appear in any "recent" lists at the OS level, or within any applications.

You could "hide" an actual physical document / letter somewhere, and the delayed email could tell them where to find it.

There is also http://www.letter2future.com but I haven't really looked into it, and can't vouch for its reliability. Also, I don't think I would want to trust it in privacy terms. However, perhaps it could be used to tell someone where to find the actual hidden letter or document, or to remind someone to check their emails, eg in order to find the two emails for the encrypted document scheme explained in the first post.

Another approach would be to send an encrypted document in the scheduled email, but for the password to be stored somewhere where the recipient can access it. The email would tell the recipient where they can find the password.

 

[benjaminbusdriver]

If the dropbox link were not publicly accessible, but were only accessible by the recipient (and perhaps a limited group of other people), then I think that would be okay, provided the company providing the scheduled email service is not the same company providing the file hosting.

If the dropbox link were publicly accessible, then it brings me back to considering that we don't really know what scanning tools they may or may not have. Also, could there be a possibility of manual checking for future scheduled emails ?
Personally I don't know if I would feel comfortable with "hoping" that those don't apply.
I would want something I *know* is fairly watertight.
The encrypted document scheme explained in the first post offers that.

There could be other approaches.....

You could "hide" a document somewhere on the recipients machine, and the delayed email could tell them where to find it. In that case you would want to ensure the document does not appear in any "recent" lists at the OS level, or within any applications.

You could place a document on a USB key, and the delayed email could tell them where to find it. Again, ensure the document does not appear in any "recent" lists at the OS level, or within any applications.

You could "hide" an actual physical document / letter somewhere, and the delayed email could tell them where to find it.

There is also http://www.letter2future.com but I haven't really looked into it, and can't vouch for its reliability. Also, I don't think I would want to trust it in privacy terms. However, perhaps it could be used to tell someone where to find the actual hidden letter or document, or to remind someone to check their emails, eg in order to find the two emails for the encrypted document scheme explained in the first post.

Another approach would be to send an encrypted document in the scheduled email, but for the password to be stored somewhere where the recipient can access it. The email would tell the recipient where they can find the password.

Good points. My Dropbox link would be only for the email recipient. The document is a PDF with a password inside a private Dropbox folder. Password is emailed from a 2nd gmail account. Time delay would be same for both. I think this could work. Thanks for your input.

 

[jgm63]

This thread was asking about sending messages to ER/LE (emergency response / law enforcement)

I suppose one concern might be : Would ER/LE go to the bother of fetching the password from one email and using it to open the document in the other email ? Especially if the process does not go 100% smoothly, eg if one of the emails goes into the "spam" folder for some reason, etc, etc.

I think the best approach might simply be to follow the main method in the first post of this thread, but send the email to a person you know, and ask *them* to contact ER/LE.... Perhaps send to multiple people to try to ensure at least one of them sees the email. Alternatively you could perhaps find an organisation or help/support group to send the email to, and ask them to contact ER/LE.

Some other possible approaches (but note the assumptions listed further down) :

1) Use the gmail delayed email (or a similar service from another provider) with attached encrypted document, and simply put the password into that same email.

2) Use the delayed email with attached encrypted document, and include a very descriptive password hint, that the recipient will definitely understand. Make sure you clarify upper / lower case, whether there are any spaces, etc.

3) Upload a document somewhere (or use pastebin.com, etc), and put a link to it in a delayed email.

The above make these assumptions : 1) gmail doesn't have some sophisticated AI that will spot this, and open and scan the document for keywords 2) gmail is not doing any manual human scanning of future scheduled emails. You would have to do your own risk assessment on this.

Alternatively.....
If you have an android phone, there's an app "Do It Later", that supports delayed SMS / gmail messages.

Pros :
Good privacy (messages stored locally on phone, not on any server)
Don't need to encrypt anything or attach documents, etc.

Cons :
Phone needs enough battery power to last until messages sent (maybe leave it on charge / plugged in)
SMS would need network signal, email would need internet connection (wifi or network signal)

Those "cons" are significant, however, so people will have to decide whether they're comfortable with the risk of a message not being sent.
Also note that you should test it, including the cancel feature (I haven't personally tested it yet).
There are more notes on Do It Later in the first post of this thread under "Other options".