Switching from Outlook to Gmail takes five steps. Create the Gmail or Google Workspace account, move the mail, then move contacts and calendar separately. Set up forwarding from the old address, then rebuild what doesn’t transfer. Gmail’s built-in import brings messages but no folders. Rules, signatures and categories never migrate at all, and you rebuild those by hand.

Here’s the frame for this one: the moving truck. A truck moves boxes. It does not move your shelves, your labels, or the way you had things arranged.

Every migration guide I read treats this like one button press. It isn’t, and the gap between what the truck carries and what it leaves behind is where people lose data.

So let’s load the truck properly.

What Moves Automatically, and What You Rebuild by Hand

Start here, because this table decides how much manual work you’re signing up for. Everything in it comes from Google’s and Microsoft’s own documentation.

Item	Moves automatically?	Source and detail
Email messages	Yes	Google’s import brings messages; the Workspace data import tool skips anything over 150 MB
Folders	No, for the consumer import	Google states you can import messages “but not any folders or labels”
Folders, admin migration	Yes, as labels	Google converts each folder’s full path into a label name
Contacts	Partly	Google Contacts imports CSV and vCard, 3,000 per batch, 25,000 total
Calendar	Manually, via ICS	Google Calendar caps import files at 1 MB
Outlook rules	No	Google says to create equivalent filters in Gmail
Signatures	No	Google states signatures can be re-created in Gmail
Categories	No	Google lists category definitions and assignments as unsupported
Flags	Depends on the tool	Google’s two migration tools document opposite outcomes, covered below
Guests on calendar events	No	Google states guests and conference data are not imported

Three Things That Changed Recently, and Most Guides Missed All Three

1. You Can No Longer Add an Outlook Account to Gmail on a Computer

This one breaks the standard advice outright. Google states it plainly: “In Gmail on your computer, you can no longer add an Outlook account.”

Google’s stated cause is Microsoft requiring modern authentication from non-Microsoft email clients. Google’s documented workaround is the Gmail mobile app, where you add the account under “Outlook, Hotmail, and Live.”

Wait, so the desktop route just went away? For adding an Outlook account, yes. The one-time import covered in step 2 still works on the web.

2. Gmail’s “Check Mail From Other Accounts” Is Being Retired

Google has published an end date for the POP-based fetch feature that most switching guides recommend as the gradual option.

“After the first quarter of 2026, this feature no longer supports new users. Existing users can still use the feature until January 2027.”

Source: Google, “Check mail from other accounts” deprecation notice

Gmailify goes on the same schedule. Google’s recommended replacements are forwarding set up at the source provider, or the Gmail mobile app over IMAP.

Google confirms the one-time import survives: you can still import mail and contacts on the web, but it’s a one-time move with no continuous sync.

3. New Outlook Exports a PST but Cannot Import One

This asymmetry is documented in a single Microsoft article and it catches people out. New Outlook for Windows can export a PST. It can’t import one back.

Microsoft’s export page, ms.date 05/06/2026, lists New Outlook for Windows under Applies To and gives the path Settings, Files, Export. The same page then says importing a mailbox or calendar from a PST “is currently not supported in new Outlook at this time.”

There’s a second limit on that export. Microsoft says calendar and contacts items saved in PST files are “not available in new Outlook at this time.” A new Outlook PST is mail only.

Practical consequence: if new Outlook is all you have, you can produce a PST you cannot restore without installing classic Outlook. Plan the contacts and calendar exports separately, as CSV and ICS.

Why Switch From Outlook to Gmail?

Both clients are good, and the reasons to move are usually search, cost and platform gravity. Gmail’s search handles operator combinations that Outlook makes you build a Search Folder for.

Cost matters if you’re leaving a paid Microsoft plan and your team already lives in Google Docs and Drive. Our comparison of Outlook vs. Gmail and the older G Suite vs. Office 365 breakdown both go deeper than this page will.

Say plainly what you’re giving up. Outlook’s rules engine is more capable than Gmail filters, and a writer at ZDNet found that those filters are not always reliable as a replacement.

Step 1: Set Up the Gmail or Google Workspace Account

Decide first whether you need a personal Gmail address or a Google Workspace account on your own domain. Workspace is what you want if you’re moving a business, and Google documents how to sign up for Google Workspace.

Workspace also unlocks the admin migration tools in step 2. A personal Gmail account can only use the consumer import, which is more limited.

One admin prerequisite catches Workspace teams out. An administrator has to switch on user email uploads under Apps, Google Workspace, Gmail, Setup before anyone sees the import option. Google says the change “can take up to 24 hours but typically happen more quickly.”

Step 2: Move Your Email

There are three routes, and which one you use depends on whether you’re moving one mailbox or a company.

Route A: Gmail’s Built-In Import, for a Single Mailbox

In Gmail, open Settings, See all settings, then the Accounts and Import tab, then Import mail and contacts. Google’s documentation for this sits on its automatically forward messages and import help page.

Two documented behaviors are worth knowing before you start. Google forwards messages sent to your other account for 30 days after the import. Your new Gmail address stays visible for 60 days, or until you delete the reminder.

The big caveat is structural. Google states you can import messages from another account, “but not any folders or labels.” Everything lands flat.

Google’s import also runs over POP and can’t read a PST file. I checked the import page and its troubleshooting page. Neither mentions PST anywhere, and the documented flow has no file picker.

Route B: The Workspace Data Import Tool, for a Company

Google renamed the Data Migration Service to the data import tool, and moved the whole documentation set. Old URLs under support.google.com/a/answer/ now redirect, so any guide still saying “Data Migration Service” is citing retired paths.

It migrates email, calendar, contacts and Microsoft To Do tasks. Google’s default mode handles up to 1,000 Exchange Online users at once. The advanced mode handles 5,000 users per batch, across up to 10 batches. If the two product names still blur together, we untangle the difference between Outlook the client and Exchange the server in Microsofts own words.

This is the route that preserves folder structure. Google converts each folder’s full path into a Gmail label name, so a nested folder becomes one long label.

Outlook folder	Gmail destination
Inbox	INBOX
Sent Items	SENT
Drafts	DRAFT
Junk Email	SPAM
Deleted Items	TRASH
Archive	A custom label named Archive_
Outbox	A custom label named Outbox_
Any nested folder	A label built from the folder’s full path

Two documented traps sit inside that mapping. Folder names containing slashes become labels with underscores, so A/B/C arrives as A_B_C.

And folder paths longer than 225 characters aren’t imported at all. Deeply nested Outlook structures hit that ceiling more often than you’d guess.

Route C: A PST File, via Google’s Admin Tool

Google does document moving a PST into Google Workspace, which surprises people. The tool is Google Workspace Migration for Microsoft Exchange, and Google’s page covers migrating email, calendar or contact data from PST files.

It has requirements. Google says PST password protection has to be off. The files also need a folder-per-user structure named by primary email address, plus a control CSV.

Google also documents a quirk worth planning around. With an exported or archived PST, Google can’t identify the primary root folder. Calendars then land under Other calendars rather than as the default calendar.

Where Google’s Own Two Tools Disagree

The data import tool and Google’s desktop migration tool document three of the same rules with different outcomes. Both pages are current, so name your tool before quoting any limit.

Rule	Data import tool	Desktop migration tool
Maximum message size	Google states 150 MB	Google states 25 MB
Outlook flags	Google lists flagged status as not imported	Google says flags appear as stars in Gmail
Folder paths over 225 characters	Google says messages import without the label	Google says the messages are not migrated either

Anyone quoting “Google’s migration limit is 150 MB” without naming the tool has even odds of being wrong. That detail only shows up if you read both pages.

Step 3: Move Contacts and Calendar Separately

Neither rides along with the mail unless you’re using the admin tool, so treat them as their own job.

Contacts

Export from Outlook as CSV, then import at contacts.google.com using Import in the left rail. Google Contacts accepts CSV and vCard files.

Google publishes three numbers here. Split anything over 3,000 contacts into multiple CSVs, the account ceiling is 25,000 contacts, and each contact is capped at 128 KB.

Microsoft adds a gotcha most guides skip: make sure the CSV uses UTF-8 encoding, or non-English names arrive mangled. Once you’re in Gmail, our guide to how to export Gmail contacts covers going the other way.

Calendar, and the Failure Nobody Warns You About

This is the most likely point of failure in the whole migration, and neither vendor cross-references the other.

Microsoft’s own Outlook-to-Google-Calendar article, ms.date 01/16/2026, walks you through File, Save Calendar, and offers a “Whole calendar” date range. Its only warning is that a large range “might create a large iCalendar file.”

Google Calendar hard-caps import files at 1 MB. A whole-calendar export from a busy account sails past that, and nothing on Microsoft’s page tells you so.

Export in date-range slices instead. Google also documents two losses. Guests and conference data aren’t imported, and repeat events from a CSV arrive as separate one-time events.

Step 4: Keep the Old Outlook Account Alive, and Forward From It

Don’t close the Outlook account the day you finish. Give it months, not weeks.

Gmail’s import forwards new mail for 30 days, which buys you time and nothing more. Set up setting up permanent mail forwarding at the Outlook end so nothing depends on that window.

Six months is a reasonable holding period for a personal account, and a year is safer for a business address. Anything with an annual renewal cycle, from domains to insurance, will surface in that time.

While you’re waiting, use the time to block or flag spam addresses so you don’t carry old noise into the new inbox. If you’d rather run both for a while, our guide to how to sync Outlook with Gmail covers the overlap period.

Step 5: Rebuild What the Truck Left Behind

This is the step every four-step guide skips, and it’s where the real work is.

Rules Become Filters, by Hand

Google’s position is explicit. Rules, both server and client, aren’t migrated, and you create equivalent filters in Gmail. Write your Outlook rules down before you decommission the account.

Gmail filters are less capable than Outlook rules in some areas and better in others. Budget an afternoon rather than ten minutes.

Signatures, Categories and Read Receipts

Google states signatures can be re-created in Gmail, which is documentation-speak for “we didn’t bring them.” Category definitions and assignments are unsupported, as are read receipts and delivery reports.

Outlook categories have no true Gmail equivalent. Labels are the closest thing, and they behave differently enough that a straight mapping usually disappoints.

Labels, Which Are Not Folders

A message lives in exactly one Outlook folder. In Gmail it can carry several labels at once. That’s more flexible, and it takes about a week to stop feeling wrong.

Google’s archive feature replaces the Outlook habit of filing everything. Archiving pulls a message out of the inbox while leaving it searchable in All Mail.

Inbox Layout and Conversation View

Gmail’s category tabs split incoming mail into Primary, Social, Promotions and more. Switching them off gives you a single stream closer to what Outlook trained you to expect.

Conversation view is the other big adjustment. Gmail threads replies together by default, and Outlook users often turn it off for the first month before turning it back on.

Once you’re settled, three of our guides will get you past parity with the old setup. Start with Gmail’s extensive customization options, then Gmail’s features and our list of Gmail hacks and tricks.

How Do You Tell Whether the Move Worked?

A migration is finished when your team’s reply times are back where they were, and that takes longer than the import does. New keyboard habits and a new filing model both cost speed for a few weeks.

EmailAnalytics is a SaaS tool that visualizes team email activity in Gmail and Outlook, with a focus on how long replies take. It measures both platforms, so running it across the switch shows you the dip and the recovery instead of leaving you to guess.

Inbox layout is a productivity variable rather than a cosmetic one. Our pieces on the layouts and workflows you are used to, stay more productive, productivity-boosting hacks and Outlook vs. Gmail all come at it from different angles.

Start Here: The First Hour

1. Create the Gmail or Google Workspace account, and have an admin switch on user email uploads if you’re on Workspace.
2. Export Outlook contacts to CSV and confirm the file uses UTF-8 encoding, per Microsoft’s instruction.
3. Export the calendar to ICS in date-range slices, because Google Calendar rejects import files over 1 MB.
4. Run Gmail’s Import mail and contacts, and expect messages without folders.
5. Write down every Outlook rule before you stop paying for the account, since Google never migrates them.

Frequently Asked Questions About Switching From Outlook to Gmail

Can you import a PST file directly into Gmail?

Not through consumer Gmail. Google’s Import mail and contacts feature works over POP and has no file upload step, and neither the import page nor its troubleshooting page mentions PST at all. Google Workspace administrators can move PST data using Google Workspace Migration for Microsoft Exchange, which is a separate admin tool with its own setup requirements.

Do Outlook folders become Gmail labels?

Only through the admin migration tools. Google states that the consumer import brings messages “but not any folders or labels,” so a personal import arrives flat. The Workspace data import tool does convert folders into labels, using each folder’s full path as the label name, and it skips folder paths longer than 225 characters.

How long does Gmail forward mail from your old account?

Google forwards messages sent to your other account for 30 days after the import completes, and shows your new Gmail address for 60 days or until you delete the reminder. Thirty days is a bridge rather than a plan, so set up permanent forwarding at the Outlook end as well.

Can new Outlook export and import a PST file?

New Outlook for Windows can export a PST but can’t import one, and Microsoft documents both in the same article. Microsoft also states that calendar and contacts items in PST files are not available in new Outlook, so its export covers mail only. Importing a PST requires classic Outlook.

Is Gmail’s “check mail from other accounts” going away?

Yes. Google states the POP-based feature stopped supporting new users after the first quarter of 2026, and that existing users can continue until January 2027. Gmailify follows the same schedule, and Google points users to forwarding from the source provider or to the Gmail mobile app over IMAP.

Do Outlook rules and signatures transfer to Gmail?

No. Google lists rules, both server and client, as not migrated and says to create equivalent filters in Gmail, and it says the same about signatures. Categories, read receipts and delivery reports are also unsupported, so plan to rebuild all of them by hand.

Why does a calendar import fail when the export worked?

Google Calendar only accepts import files of 1 MB or smaller, and a whole-calendar Outlook export from a busy account usually exceeds that. Microsoft’s own guide encourages exporting the whole calendar and warns only that the file “might be large,” without mentioning Google’s cap. Export in date-range slices to stay under 1 MB.

What We Verified, and When

Every figure here was checked against Google and Microsoft documentation on 4 August 2026. Microsoft pages carry a real per-article ms.date, which is quoted where relevant, and Google’s consumer help pages carry no date at all.

One limitation to state plainly. Microsoft’s PST export article hides its classic Outlook steps in a tab that doesn’t render in a plain fetch, so the exact classic click path here is drawn from Microsoft’s contacts and import articles instead.