diff --git a/proto/src/internal/error.rs b/proto/src/internal/error.rs
index 63934e85e..fd2c2bac1 100644
--- a/proto/src/internal/error.rs
+++ b/proto/src/internal/error.rs
@@ -151,6 +151,7 @@ pub enum OperationError {
     MG0003ServerPhaseInvalidForMigration,
     MG0004DomainLevelInDevelopment,
     MG0005GidConstraintsNotMet,
+    MG0006SKConstraintsNotMet,
     //
     KP0001KeyProviderNotLoaded,
     KP0002KeyProviderInvalidClass,
@@ -302,6 +303,7 @@ impl OperationError {
             Self::DB0002MismatchedRestoreVersion => None,
             Self::MG0004DomainLevelInDevelopment => None,
             Self::MG0005GidConstraintsNotMet => None,
+            Self::MG0006SKConstraintsNotMet => Some("Migration Constraints Not Met - Security Keys should not be present."),
             Self::KP0001KeyProviderNotLoaded => None,
             Self::KP0002KeyProviderInvalidClass => None,
             Self::KP0003KeyProviderInvalidType => None,
diff --git a/proto/src/internal/mod.rs b/proto/src/internal/mod.rs
index 74ad4d2df..947808dab 100644
--- a/proto/src/internal/mod.rs
+++ b/proto/src/internal/mod.rs
@@ -242,6 +242,9 @@ pub struct DomainUpgradeCheckReport {
 pub enum DomainUpgradeCheckStatus {
     Pass6To7Gidnumber,
     Fail6To7Gidnumber,
+
+    Pass7To8SecurityKeys,
+    Fail7To8SecurityKeys,
 }
 
 #[derive(Debug, Serialize, Deserialize, Clone)]
diff --git a/server/daemon/src/main.rs b/server/daemon/src/main.rs
index e28c174a5..482f7623c 100644
--- a/server/daemon/src/main.rs
+++ b/server/daemon/src/main.rs
@@ -221,6 +221,23 @@ async fn submit_admin_req(path: &str, req: AdminTaskRequest, output_mode: Consol
                                 info!("affected_entry         : {}", entry_id);
                             }
                         }
+                        ProtoDomainUpgradeCheckStatus::Pass7To8SecurityKeys => {
+                            info!("upgrade_item           : security key usage");
+                            debug!("from_level             : {}", item.from_level);
+                            debug!("to_level               : {}", item.to_level);
+                            info!("status                 : PASS");
+                        }
+                        ProtoDomainUpgradeCheckStatus::Fail7To8SecurityKeys => {
+                            info!("upgrade_item           : security key usage");
+                            debug!("from_level             : {}", item.from_level);
+                            debug!("to_level               : {}", item.to_level);
+                            info!("status                 : FAIL");
+                            info!("description            : Security keys no longer function as a second factor due to the introduction of CTAP2 and greater forcing PIN interactions.");
+                            info!("action                 : Modify the accounts in question to remove their security key and add it as a passkey or enable TOTP");
+                            for entry_id in item.affected_entries {
+                                info!("affected_entry         : {}", entry_id);
+                            }
+                        }
                     }
                 }
             }
diff --git a/server/lib/src/credential/mod.rs b/server/lib/src/credential/mod.rs
index 84960d28b..7c30597e2 100644
--- a/server/lib/src/credential/mod.rs
+++ b/server/lib/src/credential/mod.rs
@@ -645,6 +645,13 @@ impl Credential {
         }))
     }
 
+    pub(crate) fn has_securitykey(&self) -> bool {
+        match &self.type_ {
+            CredentialType::PasswordMfa(_, _, map, _) => !map.is_empty(),
+            _ => false,
+        }
+    }
+
     /// Get a reference to the contained webuthn credentials, if any.
     pub fn securitykey_ref(&self) -> Result<&Map<String, SecurityKey>, OperationError> {
         match &self.type_ {
diff --git a/server/lib/src/server/migrations.rs b/server/lib/src/server/migrations.rs
index 2110fc042..5392ae25e 100644
--- a/server/lib/src/server/migrations.rs
+++ b/server/lib/src/server/migrations.rs
@@ -797,6 +797,39 @@ impl<'a> QueryServerWriteTransaction<'a> {
             return Err(OperationError::MG0004DomainLevelInDevelopment);
         }
 
+        // ============== Apply constraints ===============
+        let filter = filter!(f_and!([
+            f_eq(Attribute::Class, EntryClass::Account.into()),
+            f_pres(Attribute::PrimaryCredential),
+        ]));
+
+        let results = self.internal_search(filter)?;
+
+        let affected_entries = results
+            .into_iter()
+            .filter_map(|entry| {
+                if entry
+                    .get_ava_single_credential(Attribute::PrimaryCredential)
+                    .map(|cred| cred.has_securitykey())
+                    .unwrap_or_default()
+                {
+                    Some(entry.get_display_id())
+                } else {
+                    None
+                }
+            })
+            .collect::<Vec<_>>();
+
+        if !affected_entries.is_empty() {
+            error!("Unable to proceed. Not all entries meet gid/uid constraints.");
+            for sk_present in affected_entries {
+                error!(%sk_present);
+            }
+            return Err(OperationError::MG0006SKConstraintsNotMet);
+        }
+
+        // =========== Apply changes ==============
+
         Ok(())
     }
 
@@ -1095,6 +1128,19 @@ impl<'a> QueryServerReadTransaction<'a> {
             report_items.push(item);
         }
 
+        if current_level <= DOMAIN_LEVEL_7 && upgrade_level >= DOMAIN_LEVEL_8 {
+            let item = self
+                .domain_upgrade_check_7_to_8_security_keys()
+                .map_err(|err| {
+                    error!(
+                        ?err,
+                        "Failed to perform domain upgrade check 7 to 8 - security-keys"
+                    );
+                    err
+                })?;
+            report_items.push(item);
+        }
+
         Ok(ProtoDomainUpgradeCheckReport {
             name,
             uuid,
@@ -1191,6 +1237,45 @@ impl<'a> QueryServerReadTransaction<'a> {
             affected_entries,
         })
     }
+
+    pub(crate) fn domain_upgrade_check_7_to_8_security_keys(
+        &mut self,
+    ) -> Result<ProtoDomainUpgradeCheckItem, OperationError> {
+        let filter = filter!(f_and!([
+            f_eq(Attribute::Class, EntryClass::Account.into()),
+            f_pres(Attribute::PrimaryCredential),
+        ]));
+
+        let results = self.internal_search(filter)?;
+
+        let affected_entries = results
+            .into_iter()
+            .filter_map(|entry| {
+                if entry
+                    .get_ava_single_credential(Attribute::PrimaryCredential)
+                    .map(|cred| cred.has_securitykey())
+                    .unwrap_or_default()
+                {
+                    Some(entry.get_display_id())
+                } else {
+                    None
+                }
+            })
+            .collect::<Vec<_>>();
+
+        let status = if affected_entries.is_empty() {
+            ProtoDomainUpgradeCheckStatus::Pass7To8SecurityKeys
+        } else {
+            ProtoDomainUpgradeCheckStatus::Fail7To8SecurityKeys
+        };
+
+        Ok(ProtoDomainUpgradeCheckItem {
+            status,
+            from_level: DOMAIN_LEVEL_7,
+            to_level: DOMAIN_LEVEL_8,
+            affected_entries,
+        })
+    }
 }
 
 #[cfg(test)]