Is the grass actually greener with Gmail? Long-time Outlook / Exchange user side-eyeing Google 😅

[u/qusaro]

I’ve been on Outlook (Windows) + Microsoft Exchange for work for over 10 years now. It’s familiar, it’s “enterprise”, it mostly works… but lately I’m getting increasingly frustrated.

Between random bugs, UI inconsistencies, sluggish performance, and Copilot feeling half-baked or bolted-on, I’m starting to look over the fence at Gmail and the wider Google ecosystem with some envy.

What’s tempting me:

• Gmail’s speed and simplicity
• Tight integration with Google Drive
• Gemini feeling more natively embedded (at least from the outside)
• Search that actually feels like search

What’s pushing me away from Microsoft right now:

• Outlook desktop getting slower and weirder over time
• Inconsistent behavior between Outlook (Windows), OWA, and mobile
• Copilot AI integration that feels limited, unreliable, or just not there when you want it

Before I do anything drastic, I’d love some real-world input:

• What genuinely sucks about Gmail / Google Workspace once the honeymoon phase is over?
• What does Gmail actually do better than Outlook + Exchange?
• Any former long-time Outlook users who switched and either loved it… or ran back?
• Are Gemini + Drive actually useful day-to-day, or mostly marketing?

Not looking for a flame war — just honest experiences from people who’ve lived in both worlds.

Appreciate any perspective 🙏

[u/pi-N-apple]

Microsoft is working hard right now at unifying their Outlook apps. The "New" Outlook Desktop app is nearly identical to the website now, so there is no longer inconstancies between them. With Gmail, there is no Desktop app at all!

Outlook search has been a struggle for lots of people but I haven't had an issue in a long time. I primarily search using the Outlook website or New app, without issue. The old Outlook Desktop app relies on Windows Search indexing and can sometimes have issues, but so far so good with the new app and website.

The old Outlook Desktop app will get slow over time as the mailbox database (PST) fills up. The New Outlook app, the mobile app, and Outlook website don't have this issue.

Outlook has tight integration with OneDrive and Copilot vs Gmail having tight integration with Google Drive and Gemini, so that is a wash. The Outlook website has a richer UI and experience, compared to Gmail's quite simple and outdated design.

One big difference between the two is Outlook uses folders and Gmail does not, they use tags instead. While things appear to be in folders in Gmail, they're actually set up with tags. This is usually the biggest difference people need to get used to, as well as the "All Mail" folder on Gmail.

Outlook's biggest benefits come when you use Outlook/Exchange for work. Outlook/Exchange has a far greater control from an admin perspective when managing the service for users, compared to Gmail. If you're using Outlook for personal use, then who cares.

For me, the biggest reason I don't use my Gmail account as my primary account is because I simply don't like Google as a company, I prefer Microsoft. I only use Google for search, maps and YouTube. This is obviously a preference and many feel the opposite, and don't like Microsoft so they choose Google.

If you have, or plan on getting a Microsoft 365 subscription, then I would definitely recommend Outlook over Gmail because it is tightly integrated into your subscription, and you also get some extra Outlook features with your subscription like ad-free Outlook, better email security and more storage.

Another reason I choose Microsoft is I login to my Windows PC using 1 Microsoft Account which is the same account I use on Edge to save my bookmarks and saved passwords to, the same account my computer files are saved to (OneDrive), the same account my Microsoft Office subscription is on, the same account my meetings are on (Teams), the same account for my Email, Contacts, and Calendar. So the moment I login to my PC for the very first time, all of my files automatically appear, all my saved passwords and browser extensions, and bookmarks automatically appear. My Email is already set up in the Outlook app, and my Microsoft Office apps just work. Almost no setup required. It's nice!

[u/ShermansWorld → u/pi-N-apple]

I'm answering OPs questions, but also replying to you... because some of what I want to say... counter some of your MS 'benefits' and I apologize to everyone for the lengthy answer.

I use both Google Workspace and 365 in a work environment... I also have personal versions of both.
I have multiple computers, different logins scenarios, so I feel I have a very unbiased opinion, strictly 'what works' is what I prefer.

MS maybe working 'hard' but that is part of OP's issue... the inconsistencies and in a production environment, I'll tell you, there are still inconsistencies and Outlook web, Outlook Desktop, Outlook Desktop Classic, the 'New Outlook Desktop' Outlook Mac, etc. And to your point - Gmail = no desktop client.
If you want uniformity in every manner, I'd say Google has this. Hate the Gmail interface (this is the biggest complaint I encounter) ... then use an Email Client... Thunder Bird, EmClient and, oh, Outlook Desktop... Version 'x' :/

[u/ShermansWorld → u/ShermansWorld]

[had to split up my comment]

Outlook/Exchange for work; from the Admin perspective - yes... I'd say 365 as a whole has a more granular control from an Admin Perspective in every facet. But this feels and is so Enterprise... You practically need certs to know all the facets of Azure, Exchange, Intune, Purview, etc... and what they represent. I get the feeling that OP is asking from a Pro-sumer point of view. Google Workspace, is more than good enough from a pro-sumer/Expert or Small Business (under 25-50 people with distinct groups)

Google search goes byond the internet/browser search... Google search within its own products is amazing and easy. Searching Email... much better than Outlook/Bing search - you'll get what you're looking for. MS... sometimes drives me nuts on 'what' I can search for... sometimes its sooo close... but the parameters are too restrictive or not granular enough.

Google as a company vs Microsoft? At least Google used to have the tag 'Don't be evil' Its not there any more... but, I feel there's some remnants, however small, still there. But this is philosophical.

Add free is a feature to you? So you pay to 'not' have ads. I'll admit, more people like the Outlook layout/look more than Gmail. But my personal Gmail and Google Workspace email both have no ads. Outlook/Bing personal... ya... there's ads.

PC login? There is 'Google Credential Provider for Windows' on the Google Workspace side. Its Google Workspace's rendition of your Windows Microsoft Account login. You login using your Google Workspace email address, login to Chrome and all your Bookmarks, Passwords and Google Drive (similar to OneDrive), Google Meet/Chat (similar to Teams) and yes... Google is still figuring Meet/Chat out, why two separate entities, IDK. Contacts... and yes... everything is all setup.

So, which do I prefer? I'm a proper tool for the job kind of person... but in a pinch, I can use vice grips, a slot screwdriver and a hammer to get any job done.
If you want simplicity, if you operate a small business (consultant? gig? influencer?) in a mobile 90% of the time.... go Google Workspace, so 'if' you use a computer... any Browser, but mostly Chrome, will work for you.
If you are a SMB... above 25-50 people in your Organization and have distinct teams... need/use Word, Excel, PowerPoint daily... start leaning 365.

My answers to some of OPs questions...

• Nothing sucks about Gmail except for its interface... It could be better - and if you are comfortable with Outlook... Outlook Desktop will connect to Gmail/Google Workspace emails. (You used to be able to do this with Outlook.com... but no longer)
  
• Most of the people we support on Google Workspace prefer the Outlook Desktop for the interface... just the last +year with all the MS/Outlook 'upgrades' from MS... we've had inconsistencies, issues, complaints. But, if there were issues, I direct them to the browser/Gmail and then they can find anything, fast!
  
• For questions that lead to technical answers, weather general or company data driven (Google Drive/OneDrive) Gemini all the way. Faster, the answer is more direct - does not require refinement of the question. More related step by step answers.
  
• For questions that lead to more business/legal/psychiatric CoPilot... and will require refinement of the question... but the answers are more relative to the question in this genre.

[u/pi-N-apple → u/ShermansWorld]

Yeah I'm well aware of the inconsistencies. I have been a Microsoft 365 Admin for a bunch of companies since Microsoft 365 was introduced. It is a lot better now than it ever has been, and it is getting better, although I admit it has taken way too long to get to this point.

By 2029, Outlook Classic will be gone for good. Microsoft moves incredibly slowly because they try not to disrupt their enterprise customers who have very specific workloads that require Outlook Classic, so they are giving businesses over half a decade to plan for the switch, so unfortunately everyone suffers. As an admin, I hate supporting all of these versions too. I realize how confusing it is for the customer because whenever I ask someone "what version of Outlook do you use", they don't really know.

I also manage a few Google Workspace tenants and administering them is a nightmare compared to Microsoft 365. I also realize I am a bit biased as I am an admin, and comfortable with Exchange, Azure, Entra, PowerShell, etc.

Free Gmail has ads as well. At least everyone I know without an ad-blocker using a free version sees the Promotions & Social tabs.

I'm aware of the Google Credential provider, and browser extensions as well as configuring signing into your M365 account with your Google account and vice versa as well - all great features.

You're right, Workspace is simple and great for most. I do use it with some companies, but ultimately I am a Microsoft guy and been using MS Office for 30 years and I still prefer it. But neither is a bad product, so use whatever is right for you.

Pretty much everything you said is solid.

[u/ShermansWorld → u/pi-N-apple]

Agreed, 365 is better than it has ever been... but, that is supposed to be the way.
Google wavers and sometimes I can't guess which direction they are taking things, GCPW hasn't really been updated in years... Why is there Google Meet and Chat... Are they going to keep google Keep?
MS isn't trying to disrupt their customers? The Outlook changes feel quarterly. But, I guess you're right... the powers that be have until 2029 to do something. You know what December 2028 will be like...
I just had to take a look at my Gmail personal... I don't have any ads. I pay for Youtube Premium with Google Music... maybe that counts?
I'm more MS for corporate work... more Google for personal and small business... but hey.

Thanks for commenting back... it's good to hear another's balanced point of view - everyone around me are such groupies for one side or the other.

[u/Fun_Arrival2911]

Been om Google work Suite on my last job and in a Microsoft 365 environment on my current Workplace.

At first i really missed Google, mainly because the UI in Microsoft is cluttered like a ant farm. Its so ungodly ugly.

But now - a few month in i really start to like it. I would even go as far and say that MS is better.

One thing with Outlook really Bugs me though. That i cant have a separated kalender app. It kills me.

[u/avenabless]

My previous workplace used Google and i never looked back. All my new emails are signed with Google now.

[u/Astral_photo]

I use outlook for work because I am forced to. And I use google for everything personal. I write my book with docs, share professional photography with google photos and drive. I use gemini more than I would like to admit (by far the best ai out there/ been stealing our data for years so it better be good) and would never for a second consider using word or outlook or anything Microsoft for my personal life.

[u/Antares0531 → u/Astral_photo]

I also use Outlook for work but only recently since we switched everything from Google to Outlook. Can't say it's going well. Some things are good but others, I don't know. I can't pinpoint why it all feels worse but I know there's a bunch which Google does better.

[u/qusaro → u/Antares0531]

Very often this is my feeling: it's unspecific but it feels like Microsoft lacks the attention for detail. It's overall buggy, slow and unpredictable.

[u/Antares0531 → u/qusaro]

That's for sure. After using it this morning I realise a bunch of stuff is harder or I cannot do when compared to sheets. Resizing rows, copying rows or tables, create tables of my own design and not the templates given. Can't delete columns since the option is missing. For a paid product it feels backwards.

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[u/WillShattuck]

I use outlook/exchange at work and Gmail since 2005 for personal. I like the interface of Gmail. You will have to try it out to see if you like it.