How to drag & drop from Personal email to work email

In the new Outlook, copying emails between mailboxes is supported.
However, as stated in the AI response, your organization’s IT administrator may restrict email copying, so please consult your IT administrator.
Between personal accounts, emails can be copied as shown below.
In my organization, the IT administrator has restricted only the copying of emails from personal accounts to organizational accounts (Exchange Online). (Copying from organizational accounts to personal accounts is allowed.)

As alternative methods, please consider the following:

• Forward emails from a personal account to an organizational account
• Export emails in EML format and import them into the organizational account
• Purchase a subscription such as Microsoft 365 Personal, install the traditional Outlook (Microsoft 365), and set up an environment in which PST files can be used in the new Outlook. Then, copy emails via the PST files.

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新しいOutlookではメールボックス間のメールコピーはサポートされています。
但し、AI回答が記載している通り組織のIT管理者がメールコピーを制限している場合がありますのでIT管理者に相談してみてください。
個人アカウント間では、下記の様にコピー出来ます。
私の組織の場合は、個人アカウントのメールを組織アカウント(Exchange Online)へのコピーだけIT管理者に制限されています。(組織アカウントから個人アカウントへはコピー可能です。)
代替方法としては、下記を検討してみてください。

• 個人アカウントから組織アカウントにメール転送
• ​メールをeml形式でエクスポートして、組織アカウント側でメールをインポート
• Microsoft365 Personalなどのサブスクリプションを購入して、従来のOutlook(Microsoft365)をインストールした上で新しいOutlookにてPSTファイルを利用出来る環境を構築。そして、PSTファイル経由でメールをコピー。

Hi,

The quickest way to resolve this is to revert to Classic Outlook by toggling it in Settings. It fully supports cross-account drag-and-drop, and Microsoft continues to support this feature.

Maybe exporting PST would work if the emails are in large numbers:

1. Export emails from your personal account to a PST file (File → Open & Export → Import/Export).
2. Import that PST into your work account.

I’m eager to hear back and work together to find a solution.

In the new Outlook for Windows, moving or copying items between different accounts is restricted by default for organization data protection.

Cross-account drag-and-drop (for example, from a personal account to a work account) is disabled unless an administrator explicitly enables it via Exchange Online policy. For enterprise accounts, the ItemsToOtherAccountsEnabled parameter in the relevant OwaMailboxPolicy must be set to $true for both the source and destination accounts using Set-OwaMailboxPolicy. For personal accounts, this parameter is already set to $true and managed by Microsoft.

If one of the accounts is a work (enterprise) account, only the organization’s admin can change this policy. If the admin does not enable it, drag-and-drop between the personal and work accounts will remain blocked in new Outlook. In that case, the only practical workaround is to continue using classic Outlook, where this limitation does not apply in the same way.

Summary of what is required:

1. Ensure both accounts are added in new Outlook.
2. Ask the work account’s Microsoft 365 admin to:
   • Use Set-OwaMailboxPolicy to set ItemsToOtherAccountsEnabled $true on the OWA mailbox policy applied to both accounts.
3. After the policy is applied, drag-and-drop between those accounts becomes allowed according to the organization’s configuration.

If the organization chooses not to enable this, new Outlook cannot be configured to allow drag-and-drop from personal to work; classic Outlook must be used instead.

References:

• Supported accounts in new Outlook for Windows