Please tell me what to say to Microsoft Support

I’ve ordered my new iMac 5K and will migrate all my files to it when it arrives. In my specialised work I rely on a heavily customised Word 2011; multiple investigations show that nothing else is suitable or adaptable to my needs (including, alas, Word 2016 or Word 2019). Office 2011 is a 32-bit suite and Catalina is 64-bit only. I have installed Parallels and created a Sierra guest OS within it so I can continue to run Word 2011.
Copying the Office 2011 files from one HDD to another never works; Office always acts as though it’s a new installation and requires registering, even though the computer is the same. Unfortunately, that is no longer possible. Previously, when I’ve replaced the HDD (now with an SSD), I’ve had to telephone Microsoft Support and argue with techs who aren’t aware that it is still possible to reauthorise an existing licence. It takes a couple of hours of being on hold and repeating my request to multiple people, and it’s exhausting.
To save my sanity, I need to know what phrases to use, in which order, to expedite the installation within Parallels. Would someone be willing to write me a step-by-step list of instructions on how to navigate the morass so I can get the installation authorised once more?
I will be retiring in a couple more years, and I hope that Office 2011 under Sierra within Parallels under Catalina and later will see me out.

I don’t know anything about Parallels or Catalina, and you do have the basics of an outline of the problem on your message. I’ve found it helpful when talking to tech support to make a detailed chronological list of what exactly has been going wrong from the minute the problem started. If possible, take screenshots. Write down exactly what any error messages say if you cannot take a screenshot. Be sure to include what troubleshooting you already did.

Be sure you let them know how many times you’ve already spoken with tech support; this should be the first words out of your mouth. And I’m guessing about MS, but I’ll bet like Apple and other big companies, they keep track of your prior calls with tech support. There’s probably even a job ticket on file - you can ask the techie to check so he can review the process to date.

And if you find the support person isn’t being helpful, or more likely, is incompetent, you can ask to speak to a supervisor or specialist.

I can’t think of any scripts for talking to tech support. It’s just important not to sound whiney or threatening. But again, don’t hesitate to move your problem up the ladder if necessary; it’s your right to do so.

May I suggest one of the following?
A) Install the program EasyFind (Download EasyFind 5.0).
It’s free and runs on Catalina.
Give it permission to search the whole disk in System Preferences-> Security & Privacy.
Search for Microsoft. Take note of all folders that it finds and where they are. Copy them to the same place in Sierra. Also copy the Microsoft Folder (and the applications inside) of Office 11 to the corresponding Applications folder. And good luck.
B) Make a clone of your original Sierra installation. First make sure to delete all unnecessary programs and files that you won’t need in Parallels. Then clone it to Parallels.

Thank you for your advice.
MMTalker: It’s not a “problem”; it’s a “feature”. Although MS Office can be moved, it has to be reinitialised with the product key, but Microsoft has removed that option for old software (such as Office 2011). I’ve gone through the process before on the phone, but it’s mentally exhausting trying to find the right person with the admin privileges to approve a new installation. I was hoping to cut to the chase by incanting some magic words that get me to the right technician.
Francisco: I have EasyFind already; it hadn’t occurred to me to do as you suggest. But I found the locations of the presumed licence files (see and moved them but it didn’t make a difference.
Making a clone of the original Sierra is good advice.
So I will have to fortify myself with strong cups of tea and pick up the phone.

I would focus on the specialized software needs you have… when you call refer to previous cases, then tell them you had to replace the hard drive so your version of word needs to be re-registered and that you can not upgrade. Do not go into any detail whatsoever of what you have or have not done. Just repeat that this is the same issue as the previous case and you would like it resolved the same way. If you spoke to a senior engineer (or whatever) ask them to put you through.

I’ve done similar calls to Apple and when the tech realizes that this has happened before and that they can not fix it they will be glad to pass you on.

Be patient, talk as little as possible. Use a headset. :wink:

Take notes!



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Thank you, Dave. That is excellent advice. I have retained the case number from last time, so the technician can call it up and see what was done. And it has bene recommended that I start by saying “The last time I called, I was advised that I would need to escalate my question to level 2 tech support. Someone with expertise in transferring licences. Could you transfer me?” I’ll start with that and then follow your advice. When the new iMac 5K arrives, I’ll report back on how it went.

I cannot help you with Micro$oft, but I do know that I have made OS backups with SuperDuper! that maintain nearly all licensing files—including Office 2004, 2008, and 2016. And I backed-up/re-created an HD partitioned with Parallels using SuperDuper!


Thanks. I’ll keep that in mind in case the Microsoft tech is uncooperative. But I can confirm that a bootable clone made with Carbon Copy Cloner is unable to preserve the Microsoft registration (likely because Microsoft Office uses the hard drive’s unique serial number).

I ran into this exact problem a few years ago. It’s true that the product key option no longer works, but there is an option in fine print below the product key entry area to register by phone. (Sorry, I can’t bring up that dialog screen at the moment, so can’t give you the precise wording.)

If you call the 1-8xx number given, an automated answer will give you a numeric code that you can enter by phone to reactivate the software. Be ready to write it down, as it’s long, consisting of 8 x 6-digit series for a total of 48 digits.

The code can be reused, but is exclusive to that computer (as I learned when I tried to use it to activate Word on another computer). If you need to activate the software on another computer, just go through the same procedure, and you’ll get another reusable code (a fresh set of 48 digits) exclusive to computer 2.

Record the codes somewhere that you will always have them with you when using that computer, such as in Evernote or a saved document, or in Contacts.

If MS identifies the target drive using the serial number of the hard drive, rather than the computer, this should work, even though the drives are on the same computer. If it does, it should save a lot of time and frustration. You will never again have to fight with tech support, as you can always call the automated line and have the code read to you.

Hope this helps. Good luck!


Thank you, Jean, for your thoughtful suggestions. Unfortunately, Microsoft has removed that option now. Instead, on entering the correct product key and being told it’s invalid, I get a link to a further series of hoops to jump through, which ultimately fails to show any telephone numbers (they really don’t want you to call). Fortunately, I took a screenshot last time, which shows the 1800 number for Australia (1800 642 008 or 13 20 58, if anyone needs it).

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Oh, dear. I haven’t needed to do this since my laptop died last fall and wasn’t aware of the change in procedure. Thanks for bringing me up to date. Sorry I couldn’t help.

When I got a new MPB, I used the Apple migration software to migrate the old HD to the new machine, and as far as I remember MS Office 2008 migrated with license, I think I did this also when I updated the HD and OS on my wife’s MBP (with Office 2019?). I didn’t have to do a thing about the MS license. Now since you don’t need the whole HD migrated, I don’t know how to specify in the migration software what not to migrate, but i guess you can 1) migrate the whole older drive, then delete a bunch of stuff if you have room on the Parallels virtual drive, or 2) clone the old drive, then delete unnecessary stuff on the old drive where Office works, then migrate 3) migrate the old drive to a spare drive, make sure Office works on it, then delete unnecessary stuff, then migrate to the new computer.