A Frustrating Journey: Microsoft 365 Business Edition Sign-Up Woes

If you’re like me, you probably have a love-hate relationship with Microsoft by now. When I first started using computers in 1997, MS-DOS was still in use. Although I was good at it, I disliked its command-line interface (CLI). Fortunately, Windows 3.1 was already available, making MS-DOS somewhat tolerable. Then came Windows 95, which promised plug-and-play functionality, though in reality, it often felt more like “plug-and-pray.” Windows 98 Second Edition improved things, but Windows ME was a disaster. Windows 2000 gained popularity in businesses, while home users stuck with Windows 98 SE until Windows XP, which became a fan favorite. It was followed by Windows Vista, an OS many users passionately disliked. Eventually, Microsoft redeemed itself with Windows 7, and later, Windows 10, both of which I liked. I haven’t used Windows 11, though, since I switched to macOS.

In 2025, Microsoft has fully embraced cloud computing, making services like Microsoft 365 central to its ecosystem. Businesses and individuals rely on its cloud tools for email, collaboration, and storage. Despite these advancements, navigating Microsoft’s systems can still be frustrating. Signing up for a subscription should be simple, yet the process often presents unexpected obstacles and confusing steps. This post focuses on the sign-up process, not the setup or daily management of Microsoft 365, which has its own challenges. You’d expect entering payment details and a few clicks would suffice, but that’s not the case. I’ll share my experience signing up for Microsoft 365 Business Basic and Standard, highlighting two key issues I faced and the workarounds I found. If you’re considering a subscription or have faced similar frustrations, this post is for you.

Note: Subscribe to my tri-monthly newsletter to receive an exclusive link to sign up for Microsoft 365 Business at a reduced rate: Business Basic at $2.40, Business Standard at $8.20, and Business Premium at $19.75. Don’t miss out—click here to subscribe now to secure your spot and enjoy these discounted rates!

Phone Number Verification Failure

A client hired me to purchase and set up a Microsoft 365 Business Basic subscription. During the sign-up, Microsoft requires phone number verification, either through an automated text or call. However, I encountered an error message: “Something is wrong with that phone number. Try a different one.” I tried multiple phone numbers from different telecom providers and used various internet connections, but none worked. After spending hours on the phone with Microsoft Support without resolution, I conducted further research. It turns out the verification fails due to Microsoft’s fraud detection system flagging my IP address. This made sense, as many dynamic IP addresses assigned by ISPs are linked to botnets involved in illegal activities. Ultimately, I realized the issue wasn’t with the phone numbers but with my IP being flagged by Microsoft’s security measures.

This issue is not isolated. According to Kaspersky, in 2023 Sri Lanka has experienced 15 million malware-related incidents. However, this figure may be an estimate or general reference, as Kaspersky does not always provide exact numbers. Regardless, it’s a significant concern. Around 46.7% of users were targeted by local threats, which aligns with the broader trends of local threat exposure. Additionally, Sri Lanka saw 7,264 DDoS attacks in the second half of that same year, many of which were amplified by botnets. Given these statistics, it’s no wonder Microsoft flagged my IP address, even though I tried different Wi-Fi connections. Although not an ideal solution, the only way to bypass this issue was to mask my IP address. I first tried using the built-in VPN feature in Microsoft Edge, but it didn’t work for reasons I couldn’t determine. I then tried again using Opera with its VPN, and this time, it worked.

Order Confirmation Process Failure

In an unrelated note, if you encounter an issue verifying your phone number with any other service (e.g., when setting up a YouTube channel), the solution I provided above should work well. Now, let’s dive into an issue I faced just two days ago. After purchasing the Microsoft 365 Business Basic subscription for one client, I had another client interested in subscribing to Microsoft 365 Business Standard. He was currently using Microsoft 365 Personal (LKR 30,000/year) and Zoho Mail Premium with a custom domain (LKR 14,196/year), totaling LKR 44,196 annually. After evaluating his needs, I realized he could save up to LKR 16,000 per year and enjoy better features by switching to Microsoft 365 Business Standard. He was impressed and wanted to proceed. I began the purchase process and was able to verify the business phone number successfully by using a VPN.

Everything went smoothly until I attempted to confirm the payment. The screen took forever to load, and in the end, the payment failed. The error message read: “Something happened and we need some more information to verify your order. Please contact support for assistance. Error code 43881.” For two days, I tried various Credit and Debit Cards, cleared my browser cache, used different browsers in incognito mode, switched Wi-Fi connections, tried multiple devices, and even used different VPN services. Unfortunately, it was the weekend, and phone support was unavailable. I tried chat support, but the queue was long, and waiting wasn’t an option, especially since I was sick with the flu and pressed for time. I didn’t want to give up and appear unprofessional to my client. In the end, I decided to post the issue on Reddit and call it a day.

Payment Method Verification Failure

I followed the same procedure as when purchasing the Microsoft 365 Business Basic subscription—keeping the VPN active and using the same credit card. However, the payment process failed again. Searching Microsoft forums, I found others facing similar issues, but none of their solutions worked for me. The next day, I logged into the Microsoft 365 Admin Center and tried purchasing a Microsoft 365 Business Standard license through the Marketplace. Unfortunately, the transaction still didn’t go through. This time, however, the error message was more specific: “Please try again in a few minutes. We are unable to complete the verification check on your payment method at this time. (CV: oGbAtm9BTTMLxQD5.42).” Frustrated, I realized this wasn’t just a payment issue but possibly another layer of Microsoft’s fraud detection interfering with the transaction.

I reinitiated the transaction, following the same steps as before but disabling the VPN after verifying my phone number. This time, the payment went through without any issues. Clearly, using a credit card issued by a Sri Lankan bank while connected to a foreign IP address had triggered Microsoft’s fraud detection system. It’s odd because the same method had worked previously, yet this time, it was flagged. This inconsistency highlights how unpredictable Microsoft’s security measures can be. While fraud prevention is necessary, these rigid checks can create unnecessary hurdles for legitimate users. The experience was frustrating, but at least I found a workaround. If you’re facing similar payment verification failures, consider disabling your VPN before making the payment. It could save you hours of troubleshooting and dealing with unhelpful support responses, just as it did for me.

Bonus Tip: If you want to use an email address with your own domain but can’t afford Microsoft 365 Business or Google Workspace—or simply don’t need all the extra features—I recommend trying Zoho’s limited but Forever Free Plan. Also, I specialize in Google Workspace, Microsoft 365 Business, and Zoho Workplace. If you need assistance, feel free to contact me.

Wrap Up

In conclusion, the phone number verification issue I faced while purchasing a Microsoft 365 Business Basic subscription highlights a significant challenge many users may encounter when dealing with Microsoft’s fraud detection system. Despite following the correct procedure, trying various phone numbers, internet connections, and even reaching out to Microsoft Support, the problem persisted. This frustrating experience was ultimately resolved when I realized that the issue was not with the phone numbers or the sign-up process, but with my IP address being flagged by Microsoft’s security measures. Many dynamic IP addresses issued by ISPs are often linked to botnets, which can trigger fraud detection systems. This underscores the importance of being aware of the potential security challenges that come with using internet services, especially when dealing with global companies that have stringent fraud prevention protocols.

My experience with Microsoft’s payment verification process highlights a common issue where using a VPN during transactions can sometimes trigger fraud detection. This typically happens when the IP address location does not match the billing address on the credit card. Although some payments may go through without any problems, this discrepancy often leads to payment verification failures, causing frustration for users. To avoid such issues, it’s advisable to disable the VPN during the payment process, allowing for a smoother transaction. Additionally, it’s crucial to ensure that the payment method details are up-to-date and consistent with the information in your Microsoft account. Any mismatch between the two can further complicate the verification process. By taking these precautions, users can effectively bypass or prevent payment-related issues and ensure a seamless sign-up and payment experience without unnecessary delays or failures.

---

If you found this content helpful, I kindly ask you to leave your feedback in the comments section below. Sharing it on social media would also be greatly appreciated. In order to promote meaningful and respectful dialogue, I request that you use your full name when commenting. Please note that any comments containing profanity, name-calling, or a disrespectful tone will be deleted. Thank you for your understanding and participation.