RequireSenderAuthenticationEnabled

POST BODY

When a partner emailed our all-hands list, they got an NDR:
“the group only accepts messages from people in its organization or on its allowed senders list… sender not allowed.”

We’d solved this once before and didn’t capture the steps. This time we did.

Forensic summary (redacted)

group: all@[corp-redacted].com
external sender: firstname.lastname@[partner-redacted].com
symptom: NDR “sender not allowed”
root causes:
1. the group required authenticated (internal) senders only, and
2. the external wasn’t on the group’s allowed-senders list
gotcha we hit: New-MailContact failed with ProxyAddressExists — an existing MailUser already owned the external SMTP, so we reused it instead of creating a new contact

Straight line (what fixed it)

identify group by SMTP and check whether it’s a DL or a Microsoft 365 Group
locate the external as an existing MailContact/MailUser (include soft-deleted objects)
add that object to the group’s AcceptMessagesOnlyFromSendersOrMembers list
allow the group to accept external senders (keeps the allow-list in effect)
test and confirm with Message trace

Reusable runbook (PowerShell, redacted)

# 0) Connect
Connect-ExchangeOnline

# 1) Variables (edit these)
$GroupSmtp = "all@[corp-redacted].com"
$ExternalAddresses = @("firstname.lastname@[partner-redacted].com")

# 2) Resolve the group (works for DL or M365 Group)
$grp = Get-EXORecipient -Filter "PrimarySmtpAddress -eq '$GroupSmtp'"
$grp | fl Name,RecipientTypeDetails,PrimarySmtpAddress,Identity,ExternalDirectoryObjectId

# 3) Ensure each external exists as a recipient we can allow (MailContact/MailUser).
#    If already present (or soft-deleted), reuse it.
$recips = @()
foreach ($addr in $ExternalAddresses) {
  $r = Get-EXORecipient -ResultSize Unlimited -IncludeSoftDeletedRecipients `
       -Filter "PrimarySmtpAddress -eq '$addr'"
  if (-not $r) {
    try { New-MailContact -Name $addr -ExternalEmailAddress $addr | Out-Null
          $r = Get-EXORecipient -Filter "PrimarySmtpAddress -eq '$addr'" }
    catch { Write-Host "Contact already exists somewhere: $addr" }
  }
  $recips += $r
}
$recips | ft Name,RecipientTypeDetails,PrimarySmtpAddress -AutoSize

# 4) Add externals to allow-list AND allow external senders
if ($grp.RecipientTypeDetails -eq "GroupMailbox") {
  # Microsoft 365 Group (Unified Group)
  foreach ($r in $recips) {
    Set-UnifiedGroup -Identity $grp.ExternalDirectoryObjectId `
      -AcceptMessagesOnlyFromSendersOrMembers @{Add=$r.Identity}
  }
  Set-UnifiedGroup -Identity $grp.ExternalDirectoryObjectId -AllowExternalSenders:$true
  Get-UnifiedGroup -Identity $grp.ExternalDirectoryObjectId |
    fl DisplayName,PrimarySmtpAddress,AllowExternalSenders,AcceptMessagesOnlyFromSendersOrMembers
} else {
  # Distribution Group / Mail-enabled Security Group
  foreach ($r in $recips) {
    Set-DistributionGroup -Identity $grp.Identity `
      -AcceptMessagesOnlyFromSendersOrMembers @{Add=$r.Identity}
  }
  Set-DistributionGroup -Identity $grp.Identity -RequireSenderAuthenticationEnabled:$false
  Get-DistributionGroup -Identity $grp.Identity |
    fl DisplayName,PrimarySmtpAddress,RequireSenderAuthenticationEnabled,AcceptMessagesOnlyFromSendersOrMembers
}

# 5) Message trace (adjust window)
Get-MessageTrace -SenderAddress $ExternalAddresses[0] -RecipientAddress $GroupSmtp `
  -StartDate (Get-Date).AddHours(-2) -EndDate (Get-Date) |
  ft Received,Status,RecipientAddress,MessageId

Common pitfalls we saw (and how we handled them)

ProxyAddressExists on New-MailContact → an existing MailUser/Contact already holds that SMTP; reuse it (or permanently remove the soft-deleted recipient first).
group can’t be found by display name → target by SMTP with Get-EXORecipient -Filter "PrimarySmtpAddress -eq '...'".
delivery still blocked after allow-list → the DL still required authenticated senders; set RequireSenderAuthenticationEnabled:$false (DL) or AllowExternalSenders:$true (M365 Group).

Click-path (EAC, if you don’t want PowerShell)

Recipients → Contacts → add/find the partner’s contact
Recipients → Groups → open the group → Delivery management → “Accept messages from” → add the contact
For DLs: turn off “Require sender authentication”
For M365 Groups: enable “Allow external senders”

Prevention / hygiene

keep an “Authorized External Senders — all” mail-enabled security group; allow that group on the DL/M365 Group, then just add/remove partner contacts over time
document the NDR verbatim and the message trace ID when you close an incident

Redaction note

All addresses and names are redacted. Replace with your real SMTPs when running the script.

Jet Mariano

Tag: RequireSenderAuthenticationEnabled

Fixing “Sender not allowed” to an internal group (Exchange Online) — a quick forensic + runbook