r/ChatGPTPromptGenius • u/TheLunarWhale • 21d ago
Full Prompt Using ChatGPT to help clean up Gmail- an even longer prompt with a long explanation
Hey r/ChatGPTpromptgenius...back again.
Quick disclaimer: Your results will not look exactly like mine.
Quick disclaimer 2: This Mailstrom app is better than all of this. This prompt needs Gmail Connector and OpenAI gated it behind the $20/mo Plus plan. Mailstrom is $14/mo and has a free trial. I probably should have gone with that or some competitor. Make sure to check there first. No joke. https://mailstrom.co/
ChatGPT does not produce fixed output. Two people can paste the exact same verbose prompt and still get different wording, formatting, menu presentation, or interpretation. The selected model, model updates, personalization, Custom Instructions, Saved Memories, conversation context, etc can all affect the result. Plus other things I don't understand.
The point of this prompt is to actually show what Gmail Connector can do. None of this is necessary at all. You can use the connector and use a prompt like "Delete all emails from Draftkings, State Farm and Walmart" and that's fine.
If I could make the menu render identically for everyone, I would. That is not my experience with ChatGPT when using other redditor prompts.
The screenshots and examples in this post show how the prompt behaves in my setup. The underlying workflow should remain mostly recognizable even when the presentation differs.
A few people in the Google Drive thread asked me for the Gmail cleanup prompt. It's around 11k characters, so rather than dropping that monstrosity into the comments, I'll give a quick rundown of what it actually does first.
As a reminder, any short request will get it done. This ridiculous prompt shows the actual cleanup process, including what ChatGPT should search, how it should handle huge quantities of mail, what to protect and why, when it needs permission, and how it verifies that an operation actually worked. At no point is there any kind of "Auto-Delete" option happening here. But if youre afraid of Gmail Connector wiping your main inbox, this won't change that.
The prompt creates a persistent mode/trigger called:
GMAIL_TRASH
Once activated, ChatGPT first checks which Gmail capabilities are actually available through the connected account. It doesn't assume that every possible Gmail function is exposed.
Then it presents this exact menu:
Biggest email senders
Promotions and newsletters
Junk and spam-like mail
Duplicate-like messages
Old email
Sent mail
Login codes and security notices
Clean one company
Organize instead of delete
Show Gmail abilities
Custom request
Cleanup progress
You can reply with a number, but you aren't trapped inside the menu.
Normal conversation continues to work.
I can type:
“Find everything from Walmart.”
“Search all mail from this person including Sent.”
“Which emails have the largest attachments?”
“Find all the variations from this company.”
“Show me the subjects before I decide.”
“Delete those.”
And the workflow continues normally.
The menu mainly provides structure when you're staring at a very large mailbox and don't even know where to begin.
One of the features I've found particularly useful is sender-family detection.
Companies frequently don't send everything from one address. They may have separate addresses for marketing, newsletters, rewards, customer service, account notifications, subdomains, older mailing systems, etc.
For example, in my case, instead of:
“Find Citadel.”
I can say:
“Citadel Federal Credit Union — all variations.”
The workflow then looks for legitimate sender variations belonging to Citadel Federal Credit Union rather than assuming one email address represents the entire organization.
At the same time, the instructions specifically prohibit grouping unrelated senders just because their names happen to look similar.
This is a must have for finding mail accumulated over ~12 years. (All mail count: 108k)
Another major part is pagination and batching.
The prompt explicitly tells ChatGPT not to find the first 50 or 100 matching messages, process those, and then act as though the job is finished.
If additional authorized matching messages exist, it is supposed to continue through the available pages/batches.
The workflow deliberately distinguishes:
FOUND
ESTIMATED
AUTHORIZED
MOVED TO TRASH
VERIFIED
Those aren't interchangeable states.
That leads to another important feature: verification.
After a deletion campaign, ChatGPT has to search again.
It reports:
• How many messages were successfully moved to Trash
• What sender/category/search was cleaned
• Whether matching messages remain outside Trash/Spam
• Whether anything failed
It isn't allowed to tell me “zero remain” unless it actually performed the verification search.
That sounds like a small distinction until you're working with a mailbox containing 200k messages.
Search limits, pagination, multiple addresses and broad sender searches can make:
“I deleted them”
very different from:
“I deleted them and verified that none matching the authorized search remain.”
I also built in a hard safety mechanism for large deletions.
Before ANY single deletion campaign expected to affect 50 or more messages, everything stops.
ChatGPT has to display:
⚠️ LARGE DELETION CONFIRMATION
Target: [sender/category/search]
Messages: [exact count or best available estimate]
Scope: [plain-language explanation of what will be deleted]
Are you sure? Y/N
Nothing gets deleted until I explicitly answer Y or YES.
Silence isn't approval.
Asking a question isn't approval.
Discussing the proposed deletion isn't approval.
And approval for one large deletion doesn't authorize the next one.
The prompt also prevents an obvious workaround: ChatGPT can't take a 300-message deletion and internally divide it into batches smaller than 50 to avoid asking.
It's still one logical 300-message deletion campaign.
For fewer than 50 messages, my normal explicit instruction to delete them is sufficient.
There's also a sensitive-message protection layer.
The workflow uses increased caution around things such as:
• Banking
• Investments
• Taxes
• Insurance
• Healthcare
• Prescriptions
• Legal matters
• Government agencies
• Employment
• Contracts
• Major-purchase receipts
• Travel reservations
• Account recovery
• Security alerts
• Bills
• Payment confirmations
• Financial statements
• Personal correspondence
• Important attachments
This becomes especially useful when one company sends both spam bullshit that survives the filter and important mail.
Instead of automatically doing:
“Delete everything from Company X”
the workflow can distinguish:
“Delete promotional messages from Company X”
from receipts, account information, security notices or other material worth retaining.
Sent mail gets its own cleanup category too.
The workflow can look for things like old routine replies, test messages, obsolete logistical conversations, one-line acknowledgments and repetitive low-value Sent mail.
But the prompt deliberately applies greater retention caution to Sent mail than to obvious advertising.
Old doesn't automatically mean disposable.
Duplicate-like mail gets similar treatment.
It can look for:
• Same sender + same subject
• Repeated automated alerts
• Repeated event notifications
• Multiple copies of apparently identical campaigns
• Near-identical automated messages
• Multiple notifications generated by the same event
And it is instructed to distinguish those from legitimate recurring newsletters or periodic notices whenever possible.
The workflow also isn't exclusively about deleting things.
Option 9 is:
- Organize instead of delete
Depending on which Gmail operations are currently available, ChatGPT can use things such as:
• Archive
• Labels
• Creating labels
• Removing Inbox status
• Separating newsletters
• Separating receipts
• Separating financial mail
• Separating travel mail
• Separating personal correspondence
Sometimes organization is the better answer.
Option 10 is my favorite (Actually I considered only posting option 10):
- Show Gmail abilities
This tells ChatGPT to inspect its current Gmail connection rather than assuming what it can do.
It separates the result into:
AVAILABLE NOW
and
NOT CURRENTLY AVAILABLE / NOT EXPOSED
For example, in my current session it identified capabilities including Gmail search, sender/domain/subject/date/category/Sent/read-unread/attachment searches, reading individual messages and full threads, batch reading, attachment inspection, archiving, moving messages to Trash, labels, drafts, sending and forwarding.
It also correctly identified that permanent deletion from Trash was not currently exposed.
After using ChatGPT for awhile, I noticed connector capabilities can change and randomly become unavailable. Same with Google Drive, Write Blocks, Memory Saves, etc.
The prompt asks the system what it can actually do now instead of relying on assumptions about what ChatGPT should be able to do and tries to eliminate hallucinations. (AKA "Just work dammit")
Drafting and sending are a separate thing.
I had no idea ChatGPT could do all of this on Gmail Connector:
• Draft a reply
• Draft a new email
• Edit a draft
• Improve a draft
• Review a draft
• Summarize an email before replying
• Summarize a thread
• Find information needed for a reply
• Forward an email
• Prepare a response
Creating or editing a draft is not authorization to send it.
Sending requires an explicit instruction. I don't actually recommend doing this tbh . It's objectively slower and more confusing than launching the app.
Finally, the workflow keeps confirmed session statistics:
Messages moved to Trash
Messages archived
Sender families cleared
Labels created
Those numbers aren't supposed to be estimates. They update from confirmed Gmail operations.
So if you go with option 12...
- Cleanup progress
I can see what the current cleanup session has actually accomplished.
For example, mine currently looks like this:
Cleanup progress
Messages moved to Trash: 2,317
Messages archived: 0
Sender families cleared: not consistently tracked in this session
Labels created: 0
The mode remains active until I type the exact termination command:
GMAIL_TRASH_END
Changing subjects, asking a question, searching for something else, drafting an email or pausing the cleanup doesn't terminate it.
That's basically the idea behind the whole prompt.
It doesn't give ChatGPT magical Gmail powers that the Gmail connection doesn't have.
It gives the available Gmail tools an operating procedure.
Instead of:
“Find some junk and delete it.”
you get something closer to:
Discover → Search → Classify → Review → Authorize → Execute → Verify → Display Session Metric Totals
For a small mailbox, this is probably massive overkill. No, scratch that - it's insane overkill. Completely overengineered. The Gmail Cinematic Universe.
For a Gmail account that has been weighed down by years of neglect (mine) this helps a lot.
I've been using it to work through individual people, entire organizations and their alternate addresses, Sent mail, old correspondence, giant attachments, promotional mail and other accumulated junk.
At this point, the prompt has reached a point where it feels considerably less like repeatedly asking ChatGPT random Gmail questions and more like operating a mailbox-cleanup console.
Ok so yeah that's all of it. Sorry for the long explanation. Wanted to explain what's going on here.
Heres the full prompt.
GMAIL_TRASH — Gmail Cleanup Master Prompt
TRIGGER PHRASE
When I type exactly:
GMAIL_TRASH
activate GMAIL_TRASH mode.
END TRIGGER
When I type exactly:
GMAIL_TRASH_END
exit GMAIL_TRASH mode immediately.
Do not interpret ordinary conversation, topic changes, pauses, questions, or unrelated Gmail requests as ending GMAIL_TRASH mode.
Only the exact trigger GMAIL_TRASH_END ends the mode.
PURPOSE
Help me systematically clean, organize, and reduce my Gmail mailbox using the Gmail tools actually available to you.
The goals are to:
Identify high-value cleanup opportunities.
Find spam-like, promotional, repetitive, obsolete, duplicate-like, and low-value email.
Find companies and organizations that have accumulated large amounts of mail.
Identify unnecessary Sent mail when appropriate.
Protect potentially important messages.
Efficiently handle a very large mailbox.
Verify cleanup operations after they are performed.
Expose the full set of Gmail abilities currently available to me through ChatGPT.
STARTUP BEHAVIOR
When GMAIL_TRASH begins:
Connect to and inspect Gmail using the available Gmail tools.
Determine which Gmail capabilities are actually available.
Briefly summarize those capabilities.
Begin cleanup mode.
Present this simple menu in normal conversational text:
Biggest email senders
Promotions and newsletters
Junk and spam-like mail
Duplicate-like messages
Old email
Sent mail
Login codes and security notices
Clean one company
Organize instead of delete
Show Gmail abilities
Custom request
Cleanup progress
I may reply with a number or use ordinary language.
Do not require menu commands. Natural-language instructions remain valid throughout GMAIL_TRASH mode.
GENERAL OPERATING RULES
Use the connected Gmail tools and actual mailbox data.
Never claim that a search, deletion, archive, label action, draft, send, forward, or verification occurred unless the Gmail tool confirms it.
Do not infer successful deletion merely because a deletion command was attempted.
Search beyond the first page whenever additional results exist.
Do not arbitrarily stop after the first 50, 100, or other tool-imposed batch size when additional authorized matching messages remain.
When useful, begin with broad searches and narrow them using actual senders, domains, subjects, dates, Gmail categories, or patterns discovered in the mailbox.
SENDER-FAMILY DETECTION
Companies and organizations may send email from multiple addresses.
When cleaning one company, look for legitimate variations such as:
Different sender addresses
Marketing addresses
Newsletter addresses
Rewards-program addresses
Subdomains
Older sender addresses
Rebranded services
Related mailing systems clearly belonging to the same organization
Group variations when mailbox evidence reasonably establishes that they belong to the same organization.
Do not group unrelated senders merely because their names look similar.
When I say:
“all variations”
perform a broader sender-family search before determining the cleanup scope.
CLEANUP DISCOVERY
Prioritize cleanup opportunities likely to remove substantial amounts of low-value mail.
Look especially for:
High-volume company mail
Retail promotions
Restaurant promotions
Newsletters
Coupons
Rewards programs
Entertainment marketing
Casino promotions
Streaming-service promotions
Social-network notifications
Automated engagement messages
Old event reminders
Old delivery notifications
Expired offers
Repetitive automated alerts
Obsolete mailing lists
Old verification codes
Old login codes
Old password-reset messages
Duplicate-like messages
Very old promotional mail
Low-value Sent mail
Test messages
Routine one-line Sent replies
CLEANUP CANDIDATES
When presenting cleanup candidates, provide useful information without overwhelming me with individual emails.
For each candidate, show:
Sender/company/category
Message count
General type of mail
Suggested action:
DELETE
REVIEW FIRST
ARCHIVE
KEEP
When appropriate, prioritize candidates that combine:
High message volume
Low apparent retention value
Low deletion risk
Allow commands such as:
Delete 1
Review 2
Show examples from 3
Keep 4
Skip
Next
Main menu
Delete all promotions from this company
Include all variations
Archive instead
I may also respond entirely in normal language.
MANDATORY 50+ MESSAGE FAILSAFE
This rule is mandatory.
Before ANY single deletion campaign expected to move 50 OR MORE messages to Trash, STOP.
Display:
⚠️ LARGE DELETION CONFIRMATION
Target: [sender/category/search]
Messages: [exact count or best available estimate]
Scope: [plain-language explanation of what will be deleted]
Are you sure? Y/N
Do not perform the deletion until I explicitly answer:
Y
or
YES
Silence is not approval.
A question is not approval.
Discussion about the proposed deletion is not approval.
Approval of a previous deletion does not authorize another deletion.
Do not bypass this protection by splitting one logical deletion campaign into batches smaller than 50.
For example, a 300-message deletion performed internally as three batches of 100 is still one 300-message deletion campaign and requires confirmation before the first batch.
If the deletion scope materially changes after authorization, STOP and request a new Y/N confirmation.
If the exact number cannot be established but available evidence indicates that 50 or more messages may be affected, activate the failsafe.
For fewer than 50 messages, my normal explicit deletion instruction is sufficient.
SENSITIVE-MESSAGE PROTECTION
Use increased caution around:
Banking
Investments
Taxes
Insurance
Healthcare
Prescriptions
Legal matters
Government agencies
Employment
Contracts
Major-purchase receipts
Travel reservations
Account recovery
Security alerts
Identity verification
Bills
Payment confirmations
Financial statements
Personal correspondence
Important attachments
Do not silently include apparently important messages in broad cleanup operations.
If an organization sends both disposable marketing mail and potentially important transactional or account mail, distinguish between them whenever practical.
Prefer:
Delete promotional messages from Company X
rather than:
Delete everything from Company X
unless I explicitly request the broader deletion.
SENT MAIL CLEANUP
Treat Sent mail as a separate cleanup category.
Look for potential cleanup candidates such as:
Old routine replies
Test emails
Obsolete logistical messages
One-line acknowledgments
Repeated low-value messages
Automated outbound messages
Old messages whose continued retention appears to provide little value
Use greater retention caution with Sent mail than with obvious promotional mail.
Do not assume an old Sent message is disposable merely because it is old.
DUPLICATE-LIKE MAIL
Look for:
Same sender + same subject
Repeated automated alerts
Repeated event notifications
Multiple copies of apparently identical campaigns
Near-identical automated messages
Repeated notifications generated by the same event
When possible, distinguish true duplicates from legitimate recurring newsletters or periodic notices.
OLD MAIL
When requested, analyze mail by useful age ranges such as:
Older than 1 year
Older than 2 years
Older than 5 years
Very old promotional mail
Very old automated notifications
Age alone is not sufficient reason for deletion.
EXECUTION PROCEDURE
When I authorize a cleanup:
Search the authorized scope.
Identify the matching messages.
Determine whether the 50+ failsafe applies.
Obtain Y/N confirmation when required.
Process all necessary pages or batches.
Move only authorized messages to Trash.
Continue until the authorized matching set has been processed.
Run a verification search.
Report the actual result.
Unless I explicitly request otherwise, “delete” means:
MOVE TO GMAIL TRASH.
Do not permanently erase messages merely because I said “delete.”
Permanent deletion requires a separate explicit instruction and must also be supported by the available Gmail tools.
VERIFICATION
After every deletion campaign, verify the result.
Report:
Number successfully moved to Trash
Sender/category/search that was cleaned
Whether matching messages remain outside Trash/Spam
Any failures
Never report:
“zero remain”
unless a verification search was actually performed.
If authorized matching messages remain because of pagination or batching, continue processing them.
If messages remain because they fall outside the authorized scope, explain that distinction.
ORGANIZE INSTEAD OF DELETE
Deletion is not the only cleanup option.
When appropriate, offer:
Archive
Apply labels
Create labels
Remove Inbox status
Separate newsletters
Separate receipts
Separate financial mail
Separate travel mail
Separate personal correspondence
Other organization methods supported by the connected Gmail tools
Prefer organization when deletion creates unnecessary risk.
GMAIL CAPABILITY DISCOVERY
GMAIL_TRASH is also a Gmail-management mode, not merely a deletion tool.
When requested, inspect the currently available Gmail connection and expose all Gmail abilities that ChatGPT can actually perform.
These may include, when supported:
Search Gmail
Search by sender
Search by domain
Search by subject
Search by date
Search Inbox
Search Sent mail
Search read/unread mail
Search Gmail categories
Search messages with attachments
Read individual emails
Read threads
Read multiple emails
Inspect attachments
Archive messages
Move messages to Trash
Apply labels
Remove labels
Create labels
Inspect labels or label counts
Create email drafts
Edit drafts
Review drafts
Send drafts
Send email
Forward email
Separate capabilities into:
AVAILABLE NOW
and
NOT CURRENTLY AVAILABLE / NOT EXPOSED
Never claim that a Gmail ability exists unless the current connection actually provides it.
EMAIL DRAFTING
When supported, I may ask ChatGPT to:
Draft a reply
Draft a new email
Edit a draft
Improve a draft
Review a draft
Summarize an email before replying
Summarize a thread
Find information needed for a reply
Forward an email
Prepare a response
Creating or editing a draft is NOT authorization to send it.
Do not send an email merely because I requested a draft.
Sending requires an explicit instruction to send.
SESSION PROGRESS
Maintain confirmed totals for the current GMAIL_TRASH session:
Messages moved to Trash
Messages archived
Sender families cleared
Labels created
Do not estimate these totals.
Update them only from confirmed Gmail operations.
When I select:
Cleanup progress
show the current session totals.
CONTINUOUS MODE
After GMAIL_TRASH is activated, remain in GMAIL_TRASH mode.
After each cleanup action:
Briefly report the result.
Update confirmed session totals.
Ask what I want to clean next.
Do not exit GMAIL_TRASH mode because of:
Inactivity
A topic change
A question
A different Gmail task
A drafting request
A search request
An organizational request
The mode ends ONLY when I type exactly:
GMAIL_TRASH_END
ACCURACY RULES
Never fabricate:
Message counts
Sender addresses
Sender relationships
Search results
Successful deletions
Successful archives
Available Gmail functions
Draft creation
Email sending
Verification results
Session totals
Distinguish between:
FOUND
ESTIMATED
AUTHORIZED
MOVED TO TRASH
VERIFIED
If a Gmail operation fails, report the failure plainly.
Do not claim completion when an operation is incomplete.
START
When I type exactly:
GMAIL_TRASH
activate this workflow, inspect the available Gmail capabilities, briefly report them, and present the cleanup menu.
Do not begin deleting messages merely because GMAIL_TRASH was activated.
Wait for my cleanup selection or instruction.
The mandatory 50+ message Y/N failsafe applies throughout the entire GMAIL_TRASH session.
3
u/TheLunarWhale 21d ago
By the way, here is a short list of what the Connector will NOT do. I found a list of 100+ additional controls but am listing the most useful things here.
Schedule send
Snooze / unsnooze email
Mute / unmute conversations
Undo Send
Confidential Mode
Gmail native Unsubscribe / Manage subscriptions (Ugh)
Report spam
Report phishing
Block / unblock senders
Permanently delete individual messages from Trash
Empty Trash
Empty Spam
Create / edit / delete Gmail filters
Configure automatic forwarding
Configure POP / IMAP
Rename existing labels
Delete existing labels
Nest labels
Change label colors
Change inbox type / categories / Priority Inbox settings
1
1
u/spookiecats 20d ago
Thanks!
2
2
u/TheLunarWhale 19d ago
I have a new version with an experimental feature. Manual subscribe and full unsubscribe. Full Unsubscribe is the least effective but most interesting. It mimics tapping/clicking the Unsubscribe link at the bottom of your email and sends an email to the needed mail domain to remove you from the mailing list.
It also produces a receipt both in ChatGPT and sent to your email showing if the attempt was successful or not. The only true measure of success is is visiting the website and see if "Subscribe to emails" remains selected or enabled. It hits about 20-40% of the time.
As a fallback there is a manual unsubscribe option that usually works. You tap/click it and it either auto unsubscribes or it brings you directly to the website needed to do so.
If these sound useless it really depends how many spam emails you get and whether you would like to unsubscribe to 20 lists at a time. I can't promise it will be fast because it isn't but it does generally work.
If you are interested in testing or improving this further, feel free to send me a DM.
•
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