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Outlook & Email Support — Set Up & Fixed Today

Email not sending or receiving? Need a new account set up? We configure and repair Outlook, Office 365 and any email — remotely, same day, from $59.99.

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IT Cares technician setting up and fixing Outlook email
IT Cares technician — Outlook & email support across Canada
Every email platform, one team

Outlook & Email Problems We Fix

From a brand-new Office 365 mailbox to "my email just stopped working", we set it up, fix it and make it sync across every device. Pick your platform below or jump to the problem.

Outlook (Desktop)

Setup, profiles, PST/OST repair, rules, signatures, slow Outlook fixes.

Office / Microsoft 365

Mailbox setup, migration, MFA, shared mailboxes, sync across devices.

Gmail / Google Workspace

IMAP setup in Outlook, app passwords, filters, migration to or from Gmail.

Hotmail / Outlook.com / iCloud

Re-link accounts, fix login loops, recover access, set up on all devices.

Email-specific fixes

Most Common Email Issues

Each tile links to a guide or service that helps.

How It Works

Simple as a phone call. You stay in control every step of the way.

1Tell us the email problem

New setup, not sending or receiving, password loop, missing mail — we confirm exactly what's wrong.

2We connect remotely

One-time code, AnyDesk session — same level of encryption as Canadian banks.

3Fixed & tested

We send a test email both ways and sync your devices before we finish. Average session 30 minutes.

AnyDesk uses 256-bit TLS encryption — same as Canadian banks. You see every action. Disconnect anytime. We never store your password.

Email Trouble Is Almost Always Fixable in One Session

When email breaks, it feels like the world stops — invoices don't go out, the family can't reach you, and that one important message simply won't arrive. The good news is that the vast majority of Outlook and email problems come down to a small handful of causes, and almost all of them can be solved remotely in a single short session. We've fixed thousands of mailboxes since 2014, so we usually know within minutes which of the usual suspects is to blame.

"My email isn't sending or receiving"

This is the most common call we get. Behind the scenes, the cause is nearly always one of a few things: a password that expired or was recently changed, server settings (IMAP, POP or SMTP) that drifted out of sync after an update, a single oversized message jamming the outbox, a mailbox that's hit its storage limit, or a security change at the provider that quietly requires you to sign in again. We read the actual error live on your screen, correct the real cause rather than guessing, and confirm a test email travels both directions before we call it done. Many of these same issues overlap with general Windows support, so if Outlook is misbehaving alongside other apps, we tackle both at once.

Fresh setup, migration and Office 365

Setting up email correctly the first time saves a lot of future headaches. We configure any account — Office 365, Outlook.com, Gmail, Yahoo, iCloud or a custom business domain — with the right server settings, folders, signatures and synchronization, on your Windows PC, your Mac, your phone and your tablet so everything stays in step. Moving to a new provider or a new computer? We migrate your mail, contacts and calendar so nothing is left behind. For businesses building out the full platform, our dedicated Microsoft 365 service handles tenant setup, MFA, shared mailboxes and more, and our managed IT services keep it all running long-term.

When email goes to the wrong device — or stops syncing

One of the most frustrating situations is when mail works on your phone but not your laptop, or new messages show up in one place and never reach another. That's almost always a sync, account-type or duplicate-profile issue rather than anything truly lost. We line up your accounts so the same mail, contacts and calendar appear consistently everywhere. And if you've moved to a new machine, we can pair the setup with our remote help service to transfer everything cleanly. Whatever your platform, you can always reach us through the contact page or call 1 (888) 711-9428.

Why Us

IT Cares vs Big-Box Tech Support

FeatureIT CaresGeek Squad / HelloTech
Flat Session Price$59.99 CAD$99.99–$249 USD / hr
Wait TimeUnder 15 min1–5 business days
Drive to a StoreNeverOften required
Refund If Can't FixYes — full refundRarely, fine print
Canadian-BasedYes — since 2014US headquarters
Bilingual EN / FRYesEnglish only
Talk to Real HumanAlwaysScript reader
Open 7 Days, 9am–9pm ETYesLimited hours

Pricing and service details from public sources, accurate as of 2026.

Common Questions

Why is my Outlook email not sending or receiving?
The most common causes are an expired or wrong password, incorrect server settings (IMAP/POP/SMTP), a full mailbox, a stuck message jamming the outbox, or a recent provider security change that needs re-authentication. We diagnose live, fix the setting and confirm a test email goes both ways before we finish — usually in a single remote session.
Can you set up my email in Outlook for me?
Yes. We set up any account in Outlook — Office 365, Outlook.com, Gmail, Hotmail, Yahoo, iCloud or a custom business domain — with the correct IMAP/POP and SMTP settings, signatures, folders and sync, on Windows, Mac, phone and tablet so it all stays in sync. Flat $59.99 remote session.
Do you support Office 365 / Microsoft 365 email?
Absolutely. We handle Microsoft 365 mailbox setup, migration from an old provider, shared mailboxes, aliases, distribution lists, MFA and sync across Outlook, the web and mobile. For full business deployments, see our Microsoft 365 service.
My emails disappeared or won't sync. Can you recover them?
Usually yes. Missing email is often a sync, folder-view or filter problem rather than true deletion, and we can restore the view or re-sync the account to bring everything back. If items were deleted, we check the recoverable-items store and server retention. We assess before promising anything and are honest about what can and cannot be recovered.
How much does Outlook and email support cost?
Flat $59.99 CAD for a 30-minute remote session, which covers most setup and not-sending/receiving fixes. A 60-minute session is $99.99 for migrations or multiple accounts, and priority SOS is $129.99. No diagnostic fee, and a full refund if we can't resolve it.
Is remote email support safe?
Yes. We connect over AnyDesk, which uses 256-bit TLS encryption — the same standard as Canadian banks. You give a one-time code, watch every action on your own screen, and can disconnect anytime. We never store your email password, and you can change it after the session if you wish.
Why does Outlook keep asking for my password?
A repeated password prompt usually means cached credentials have gone stale, an app password or MFA needs setting up, or the provider has changed its authentication method. We clear the bad credentials, set up modern authentication or an app password correctly, and the loop stops — typically in 15 to 30 minutes.
Can you move my email to a new computer or provider?
Yes. We migrate your mail, contacts, calendar and rules to a new computer or a new provider — for example from an old POP account or Hotmail into Microsoft 365 or Gmail — and make sure nothing is lost. We set up the same account across all your devices so the transition is seamless.
Do you fix email on phones and tablets too?
Yes. We set up and fix email in the Outlook app and the built-in Mail app on iPhone, iPad and Android, and make sure it stays in sync with your computer. If mail works on one device but not another, that's exactly the kind of mismatch we sort out in a single session.

Email Acting Up? Let's Fix It Today.

Outlook & Office 365 experts. Available 7 days a week, 9am–9pm ET.

1 (888) 711-9428 Book Session

Also see: Windows SupportMicrosoft 365Remote Help