diff --git a/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/di/BillingModule.kt b/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/di/BillingModule.kt
index 41bb945ffe..78d66bca45 100644
--- a/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/di/BillingModule.kt
+++ b/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/di/BillingModule.kt
@@ -13,6 +13,7 @@ import com.x8bit.bitwarden.data.billing.repository.BillingRepositoryImpl
 import com.x8bit.bitwarden.data.platform.datasource.disk.SettingsDiskSource
 import com.x8bit.bitwarden.data.platform.manager.FeatureFlagManager
 import com.x8bit.bitwarden.data.platform.manager.PushManager
+import com.x8bit.bitwarden.data.platform.repository.EnvironmentRepository
 import com.x8bit.bitwarden.data.vault.repository.VaultRepository
 import dagger.Module
 import dagger.Provides
@@ -57,6 +58,7 @@ object BillingModule {
         settingsDiskSource: SettingsDiskSource,
         vaultRepository: VaultRepository,
         featureFlagManager: FeatureFlagManager,
+        environmentRepository: EnvironmentRepository,
         pushManager: PushManager,
         clock: Clock,
         dispatcherManager: DispatcherManager,
@@ -66,6 +68,7 @@ object BillingModule {
         settingsDiskSource = settingsDiskSource,
         vaultRepository = vaultRepository,
         featureFlagManager = featureFlagManager,
+        environmentRepository = environmentRepository,
         pushManager = pushManager,
         clock = clock,
         dispatcherManager = dispatcherManager,
diff --git a/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManager.kt b/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManager.kt
index cee77c5b43..c652d43c37 100644
--- a/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManager.kt
+++ b/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManager.kt
@@ -38,6 +38,18 @@ interface PremiumStateManager {
      */
     val subscriptionStatusStateFlow: StateFlow<SubscriptionStatusState>
 
+    /**
+     * Emits whether the current state should be treated as self-hosted for premium upgrade
+     * gating. Reactive equivalent of [isSelfHosted].
+     */
+    val isSelfHostedFlow: StateFlow<Boolean>
+
+    /**
+     * `true` when the current state should be treated as self-hosted for premium upgrade
+     * gating, or `false` otherwise.
+     */
+    val isSelfHosted: Boolean
+
     /**
      * Returns `true` when the in-app upgrade flow is available, or `false` otherwise.
      */
diff --git a/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManagerImpl.kt b/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManagerImpl.kt
index fdec63a03f..2deecfe21a 100644
--- a/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManagerImpl.kt
+++ b/app/src/main/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManagerImpl.kt
@@ -3,6 +3,7 @@ package com.x8bit.bitwarden.data.billing.manager
 import com.bitwarden.core.data.manager.dispatcher.DispatcherManager
 import com.bitwarden.core.data.manager.model.FlagKey
 import com.bitwarden.core.data.repository.model.DataState
+import com.bitwarden.data.repository.model.Environment
 import com.x8bit.bitwarden.data.auth.datasource.disk.AuthDiskSource
 import com.x8bit.bitwarden.data.auth.datasource.disk.model.UserStateJson
 import com.x8bit.bitwarden.data.auth.repository.util.activeUserIdChangesFlow
@@ -13,6 +14,7 @@ import com.x8bit.bitwarden.data.billing.repository.model.SubscriptionStatusState
 import com.x8bit.bitwarden.data.platform.datasource.disk.SettingsDiskSource
 import com.x8bit.bitwarden.data.platform.manager.FeatureFlagManager
 import com.x8bit.bitwarden.data.platform.manager.PushManager
+import com.x8bit.bitwarden.data.platform.repository.EnvironmentRepository
 import com.x8bit.bitwarden.data.platform.util.isActive
 import com.x8bit.bitwarden.data.platform.util.scanPairs
 import com.x8bit.bitwarden.data.vault.repository.VaultRepository
@@ -47,6 +49,7 @@ class PremiumStateManagerImpl(
     private val settingsDiskSource: SettingsDiskSource,
     vaultRepository: VaultRepository,
     private val featureFlagManager: FeatureFlagManager,
+    private val environmentRepository: EnvironmentRepository,
     pushManager: PushManager,
     private val clock: Clock,
     dispatcherManager: DispatcherManager,
@@ -140,6 +143,20 @@ class PremiumStateManagerImpl(
                 initialValue = false,
             )
 
+    override val isSelfHostedFlow: StateFlow<Boolean> =
+        combine(
+            environmentRepository.environmentStateFlow,
+            featureFlagManager.getFeatureFlagFlow(FlagKey.DebugDisableSelfHostPremiumCheck),
+        ) { environment, isDebugBypassEnabled ->
+            environment is Environment.SelfHosted && !isDebugBypassEnabled
+        }
+            .stateIn(
+                scope = unconfinedScope,
+                started = SharingStarted.Eagerly,
+                initialValue = environmentRepository.environment is Environment.SelfHosted &&
+                    !featureFlagManager.getFeatureFlag(FlagKey.DebugDisableSelfHostPremiumCheck),
+            )
+
     /**
      * Eligibility is keyed on the user holding personal Premium (or being eligible to purchase
      * it). Organization-granted Premium does not surface the Plan row, since the user has no
@@ -242,6 +259,8 @@ class PremiumStateManagerImpl(
             .launchIn(unconfinedScope)
     }
 
+    override val isSelfHosted: Boolean get() = isSelfHostedFlow.value
+
     override fun isInAppUpgradeAvailable(): Boolean =
         billingRepository.isInAppBillingSupportedFlow.value &&
             featureFlagManager.getFeatureFlag(FlagKey.MobilePremiumUpgrade)
diff --git a/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanViewModel.kt b/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanViewModel.kt
index 6dbc8238c5..5798230e94 100644
--- a/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanViewModel.kt
+++ b/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanViewModel.kt
@@ -6,7 +6,6 @@ import androidx.annotation.StringRes
 import androidx.lifecycle.SavedStateHandle
 import androidx.lifecycle.viewModelScope
 import com.bitwarden.core.data.util.toFormattedDateStyle
-import com.bitwarden.data.repository.model.Environment
 import com.bitwarden.data.repository.util.baseWebVaultUrlOrDefault
 import com.bitwarden.ui.platform.base.BaseViewModel
 import com.bitwarden.ui.platform.manager.intent.model.AuthTabData
@@ -82,7 +81,7 @@ class PlanViewModel @Inject constructor(
             ?.isPremium == true
         val showsPremiumView = isPremium ||
             premiumStateManager.subscriptionStatusStateFlow.value.isPremiumViewEligible()
-        val isSelfHosted = environmentRepository.environment is Environment.SelfHosted
+        val isSelfHosted = premiumStateManager.isSelfHosted
         PlanState(
             planMode = planMode,
             viewState = when {
diff --git a/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/settings/SettingsViewModel.kt b/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/settings/SettingsViewModel.kt
index c99e95f12a..445305bdaa 100644
--- a/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/settings/SettingsViewModel.kt
+++ b/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/settings/SettingsViewModel.kt
@@ -4,7 +4,6 @@ import androidx.annotation.DrawableRes
 import androidx.compose.material3.Text
 import androidx.lifecycle.SavedStateHandle
 import androidx.lifecycle.viewModelScope
-import com.bitwarden.data.repository.model.Environment
 import com.bitwarden.ui.platform.base.BaseViewModel
 import com.bitwarden.ui.platform.base.DeferredBackgroundEvent
 import com.bitwarden.ui.platform.resource.BitwardenDrawable
@@ -16,7 +15,6 @@ import com.x8bit.bitwarden.data.billing.manager.UPGRADED_TO_PREMIUM_LEARN_MORE_U
 import com.x8bit.bitwarden.data.platform.manager.FirstTimeActionManager
 import com.x8bit.bitwarden.data.platform.manager.SpecialCircumstanceManager
 import com.x8bit.bitwarden.data.platform.manager.model.SpecialCircumstance
-import com.x8bit.bitwarden.data.platform.repository.EnvironmentRepository
 import dagger.hilt.android.lifecycle.HiltViewModel
 import kotlinx.collections.immutable.ImmutableList
 import kotlinx.collections.immutable.toImmutableList
@@ -34,7 +32,6 @@ import javax.inject.Inject
 class SettingsViewModel @Inject constructor(
     specialCircumstanceManager: SpecialCircumstanceManager,
     firstTimeActionManager: FirstTimeActionManager,
-    environmentRepository: EnvironmentRepository,
     private val premiumStateManager: PremiumStateManager,
     savedStateHandle: SavedStateHandle,
 ) : BaseViewModel<SettingsState, SettingsEvent, SettingsAction>(
@@ -44,7 +41,7 @@ class SettingsViewModel @Inject constructor(
         autoFillCount = firstTimeActionManager.allAutofillSettingsBadgeCountFlow.value,
         vaultCount = firstTimeActionManager.allVaultSettingsBadgeCountFlow.value,
         isPlanRowEligible = premiumStateManager.isPlanRowEligibleFlow.value,
-        isSelfHosted = environmentRepository.environment is Environment.SelfHosted,
+        isSelfHosted = premiumStateManager.isSelfHostedFlow.value,
         isUpgradedToPremiumCardEligible = premiumStateManager
             .isUpgradedToPremiumCardEligibleFlow
             .value,
@@ -80,13 +77,9 @@ class SettingsViewModel @Inject constructor(
             .onEach(::sendAction)
             .launchIn(viewModelScope)
 
-        environmentRepository
-            .environmentStateFlow
-            .map {
-                SettingsAction.Internal.EnvironmentReceive(
-                    isSelfHosted = it is Environment.SelfHosted,
-                )
-            }
+        premiumStateManager
+            .isSelfHostedFlow
+            .map { SettingsAction.Internal.SelfHostedStatusReceive(isSelfHosted = it) }
             .onEach(::sendAction)
             .launchIn(viewModelScope)
 
@@ -117,13 +110,13 @@ class SettingsViewModel @Inject constructor(
             handleUpgradedToPremiumCardEligibilityReceive(action)
         }
 
-        is SettingsAction.Internal.EnvironmentReceive -> {
-            handleEnvironmentReceive(action)
+        is SettingsAction.Internal.SelfHostedStatusReceive -> {
+            handleSelfHostedStatusReceive(action)
         }
     }
 
-    private fun handleEnvironmentReceive(
-        action: SettingsAction.Internal.EnvironmentReceive,
+    private fun handleSelfHostedStatusReceive(
+        action: SettingsAction.Internal.SelfHostedStatusReceive,
     ) {
         mutableStateFlow.update {
             it.copy(isSelfHosted = action.isSelfHosted)
@@ -364,9 +357,10 @@ sealed class SettingsAction {
         ) : Internal()
 
         /**
-         * Indicates that the environment has been updated.
+         * Indicates that the effective self-hosted status for premium gating has been updated —
+         * driven by environment changes or by the debug-only self-host-bypass flag.
          */
-        data class EnvironmentReceive(
+        data class SelfHostedStatusReceive(
             val isSelfHosted: Boolean,
         ) : Internal()
     }
diff --git a/app/src/test/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManagerTest.kt b/app/src/test/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManagerTest.kt
index e9694d2568..5bb9d0146f 100644
--- a/app/src/test/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManagerTest.kt
+++ b/app/src/test/kotlin/com/x8bit/bitwarden/data/billing/manager/PremiumStateManagerTest.kt
@@ -5,6 +5,7 @@ import com.bitwarden.core.data.manager.dispatcher.FakeDispatcherManager
 import com.bitwarden.core.data.manager.model.FlagKey
 import com.bitwarden.core.data.repository.model.DataState
 import com.bitwarden.data.datasource.disk.model.EnvironmentUrlDataJson
+import com.bitwarden.data.repository.model.Environment
 import com.bitwarden.vault.DecryptCipherListResult
 import com.x8bit.bitwarden.data.auth.datasource.disk.model.AccountJson
 import com.x8bit.bitwarden.data.auth.datasource.disk.model.UserStateJson
@@ -19,6 +20,7 @@ import com.x8bit.bitwarden.data.platform.datasource.disk.util.FakeSettingsDiskSo
 import com.x8bit.bitwarden.data.platform.manager.FeatureFlagManager
 import com.x8bit.bitwarden.data.platform.manager.PushManager
 import com.x8bit.bitwarden.data.platform.manager.model.PremiumStatusChangedData
+import com.x8bit.bitwarden.data.platform.repository.util.FakeEnvironmentRepository
 import com.x8bit.bitwarden.data.vault.datasource.sdk.model.createMockCipherListView
 import com.x8bit.bitwarden.data.vault.repository.VaultRepository
 import com.x8bit.bitwarden.data.vault.repository.model.VaultData
@@ -66,6 +68,7 @@ class PremiumStateManagerTest {
     }
 
     private val mutableMobilePremiumUpgradeFlagFlow = MutableStateFlow(true)
+    private val mutableDebugDisableSelfHostPremiumCheckFlagFlow = MutableStateFlow(false)
     private val featureFlagManager: FeatureFlagManager = mockk {
         every {
             getFeatureFlagFlow(FlagKey.MobilePremiumUpgrade)
@@ -73,8 +76,16 @@ class PremiumStateManagerTest {
         every {
             getFeatureFlag(FlagKey.MobilePremiumUpgrade)
         } answers { mutableMobilePremiumUpgradeFlagFlow.value }
+        every {
+            getFeatureFlag(FlagKey.DebugDisableSelfHostPremiumCheck)
+        } answers { mutableDebugDisableSelfHostPremiumCheckFlagFlow.value }
+        every {
+            getFeatureFlagFlow(FlagKey.DebugDisableSelfHostPremiumCheck)
+        } returns mutableDebugDisableSelfHostPremiumCheckFlagFlow
     }
 
+    private val fakeEnvironmentRepository = FakeEnvironmentRepository()
+
     private val dispatcherManager = FakeDispatcherManager()
 
     private val mutablePremiumStatusChangedFlow =
@@ -89,6 +100,7 @@ class PremiumStateManagerTest {
         settingsDiskSource = fakeSettingsDiskSource,
         vaultRepository = vaultRepository,
         featureFlagManager = featureFlagManager,
+        environmentRepository = fakeEnvironmentRepository,
         pushManager = pushManager,
         clock = fixedClock,
         dispatcherManager = dispatcherManager,
@@ -365,6 +377,75 @@ class PremiumStateManagerTest {
         assertFalse(manager.isInAppUpgradeAvailable())
     }
 
+    @Test
+    fun `isSelfHosted should return false on cloud environment regardless of flag`() {
+        fakeEnvironmentRepository.environment = Environment.Us
+        val manager = createManager()
+        mutableDebugDisableSelfHostPremiumCheckFlagFlow.value = false
+        assertFalse(manager.isSelfHosted)
+        mutableDebugDisableSelfHostPremiumCheckFlagFlow.value = true
+        assertFalse(manager.isSelfHosted)
+    }
+
+    @Test
+    fun `isSelfHosted should return true on self-hosted environment when flag is disabled`() {
+        fakeEnvironmentRepository.environment = Environment.SelfHosted(
+            environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
+        )
+        mutableDebugDisableSelfHostPremiumCheckFlagFlow.value = false
+        val manager = createManager()
+        assertTrue(manager.isSelfHosted)
+    }
+
+    @Test
+    fun `isSelfHosted should return false on self-hosted environment when flag is enabled`() {
+        fakeEnvironmentRepository.environment = Environment.SelfHosted(
+            environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
+        )
+        mutableDebugDisableSelfHostPremiumCheckFlagFlow.value = true
+        val manager = createManager()
+        assertFalse(manager.isSelfHosted)
+    }
+
+    @Test
+    fun `isSelfHostedFlow should emit false on cloud environment regardless of flag`() = runTest {
+        fakeEnvironmentRepository.environment = Environment.Us
+        val manager = createManager()
+        manager.isSelfHostedFlow.test {
+            assertFalse(awaitItem())
+            mutableDebugDisableSelfHostPremiumCheckFlagFlow.value = true
+            expectNoEvents()
+        }
+    }
+
+    @Test
+    fun `isSelfHostedFlow should emit true on self-hosted environment when flag is disabled`() =
+        runTest {
+            fakeEnvironmentRepository.environment = Environment.SelfHosted(
+                environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
+            )
+            val manager = createManager()
+            manager.isSelfHostedFlow.test {
+                assertTrue(awaitItem())
+            }
+        }
+
+    @Test
+    fun `isSelfHostedFlow should re-emit when debug-disable flag toggles on self-hosted env`() =
+        runTest {
+            fakeEnvironmentRepository.environment = Environment.SelfHosted(
+                environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
+            )
+            val manager = createManager()
+            manager.isSelfHostedFlow.test {
+                assertTrue(awaitItem())
+                mutableDebugDisableSelfHostPremiumCheckFlagFlow.value = true
+                assertFalse(awaitItem())
+                mutableDebugDisableSelfHostPremiumCheckFlagFlow.value = false
+                assertTrue(awaitItem())
+            }
+        }
+
     @Test
     fun `dismissPremiumUpgradeBanner should store dismissed state for active user`() {
         val manager = createManager()
diff --git a/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanViewModelTest.kt b/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanViewModelTest.kt
index 39cccd18d3..9175781ce8 100644
--- a/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanViewModelTest.kt
+++ b/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanViewModelTest.kt
@@ -67,8 +67,10 @@ class PlanViewModelTest : BaseViewModelTest() {
     }
     private val mutableSubscriptionStatusStateFlow =
         MutableStateFlow<SubscriptionStatusState>(SubscriptionStatusState.NoSubscription)
+    private var mockIsSelfHosted = false
     private val mockPremiumStateManager: PremiumStateManager = mockk {
         every { subscriptionStatusStateFlow } returns mutableSubscriptionStatusStateFlow
+        every { isSelfHosted } answers { mockIsSelfHosted }
     }
     private val mutableEnvironmentFlow = MutableStateFlow<Environment>(Environment.Us)
     private val mockEnvironmentRepository: EnvironmentRepository = mockk {
@@ -612,6 +614,7 @@ class PlanViewModelTest : BaseViewModelTest() {
 
     @Test
     fun `initial state on self-hosted should be Free SelfHosted ViewState`() = runTest {
+        mockIsSelfHosted = true
         mutableEnvironmentFlow.value = Environment.SelfHosted(
             environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
         )
@@ -633,6 +636,7 @@ class PlanViewModelTest : BaseViewModelTest() {
 
     @Test
     fun `initial state on self-hosted should not fetch pricing`() = runTest {
+        mockIsSelfHosted = true
         mutableEnvironmentFlow.value = Environment.SelfHosted(
             environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
         )
@@ -643,6 +647,36 @@ class PlanViewModelTest : BaseViewModelTest() {
         }
     }
 
+    @Test
+    fun `self-hosted with debug disable flag enabled should show Free Cloud and fetch pricing`() =
+        runTest {
+            // The PremiumStateManager helper reports false when the debug-disable flag is on,
+            // so the view model treats the self-hosted env as cloud for premium-upgrade purposes.
+            mockIsSelfHosted = false
+            mutableEnvironmentFlow.value = Environment.SelfHosted(
+                environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
+            )
+            val viewModel = createViewModel()
+
+            viewModel.stateFlow.test {
+                assertEquals(
+                    PlanState(
+                        planMode = PlanMode.Modal,
+                        viewState = PlanState.ViewState.Free.Cloud(
+                            rate = "$1.67",
+                            checkoutUrl = null,
+                            isAwaitingPremiumStatus = false,
+                        ),
+                        dialogState = null,
+                    ),
+                    awaitItem(),
+                )
+            }
+            coVerify(exactly = 1) {
+                mockBillingRepository.getPremiumPlanPricing()
+            }
+        }
+
     // endregion Self-hosted path
 
     // region Pricing fetch
diff --git a/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/settings/SettingsViewModelTest.kt b/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/settings/SettingsViewModelTest.kt
index 11b6fa4869..6e99357fac 100644
--- a/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/settings/SettingsViewModelTest.kt
+++ b/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/settings/SettingsViewModelTest.kt
@@ -2,14 +2,11 @@ package com.x8bit.bitwarden.ui.platform.feature.settings
 
 import androidx.lifecycle.SavedStateHandle
 import app.cash.turbine.test
-import com.bitwarden.data.datasource.disk.model.EnvironmentUrlDataJson
-import com.bitwarden.data.repository.model.Environment
 import com.bitwarden.ui.platform.base.BaseViewModelTest
 import com.x8bit.bitwarden.data.billing.manager.PremiumStateManager
 import com.x8bit.bitwarden.data.platform.manager.FirstTimeActionManager
 import com.x8bit.bitwarden.data.platform.manager.SpecialCircumstanceManager
 import com.x8bit.bitwarden.data.platform.manager.model.SpecialCircumstance
-import com.x8bit.bitwarden.data.platform.repository.EnvironmentRepository
 import io.mockk.every
 import io.mockk.just
 import io.mockk.mockk
@@ -44,16 +41,13 @@ class SettingsViewModelTest : BaseViewModelTest() {
 
     private val mutablePlanRowEligibleFlow = MutableStateFlow(false)
     private val mutableUpgradedToPremiumCardEligibleFlow = MutableStateFlow(false)
+    private val mutableIsSelfHostedFlow = MutableStateFlow(false)
     private val premiumStateManager: PremiumStateManager = mockk(relaxed = true) {
         every { isPlanRowEligibleFlow } returns mutablePlanRowEligibleFlow
         every {
             isUpgradedToPremiumCardEligibleFlow
         } returns mutableUpgradedToPremiumCardEligibleFlow
-    }
-    private val mutableEnvironmentFlow = MutableStateFlow<Environment>(Environment.Us)
-    private val environmentRepository: EnvironmentRepository = mockk {
-        every { environment } answers { mutableEnvironmentFlow.value }
-        every { environmentStateFlow } returns mutableEnvironmentFlow
+        every { isSelfHostedFlow } returns mutableIsSelfHostedFlow
     }
 
     @BeforeEach
@@ -332,11 +326,9 @@ class SettingsViewModelTest : BaseViewModelTest() {
     }
 
     @Test
-    fun `Plan row should be hidden when environment is self-hosted`() {
+    fun `Plan row should be hidden when self-hosted status flow emits true`() {
         mutablePlanRowEligibleFlow.value = true
-        mutableEnvironmentFlow.value = Environment.SelfHosted(
-            environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
-        )
+        mutableIsSelfHostedFlow.value = true
         val viewModel = createViewModel()
         assertFalse(
             viewModel.stateFlow.value.settingRows
@@ -345,7 +337,7 @@ class SettingsViewModelTest : BaseViewModelTest() {
     }
 
     @Test
-    fun `Plan row should update when environment changes to self-hosted`() = runTest {
+    fun `Plan row should update when self-hosted status flow flips to true`() = runTest {
         mutablePlanRowEligibleFlow.value = true
         val viewModel = createViewModel()
         assertTrue(
@@ -353,9 +345,7 @@ class SettingsViewModelTest : BaseViewModelTest() {
                 .contains(Settings.PLAN),
         )
 
-        mutableEnvironmentFlow.value = Environment.SelfHosted(
-            environmentUrlData = EnvironmentUrlDataJson.DEFAULT_US,
-        )
+        mutableIsSelfHostedFlow.value = true
         viewModel.stateFlow.test {
             assertFalse(
                 awaitItem().settingRows.contains(Settings.PLAN),
@@ -363,10 +353,29 @@ class SettingsViewModelTest : BaseViewModelTest() {
         }
     }
 
+    @Test
+    fun `Plan row should re-appear when self-hosted status flow flips back to false`() = runTest {
+        // Simulates the debug-disable flag being toggled on while self-hosted: the flow emits
+        // false even though the environment is still self-hosted.
+        mutablePlanRowEligibleFlow.value = true
+        mutableIsSelfHostedFlow.value = true
+        val viewModel = createViewModel()
+        assertFalse(
+            viewModel.stateFlow.value.settingRows
+                .contains(Settings.PLAN),
+        )
+
+        mutableIsSelfHostedFlow.value = false
+        viewModel.stateFlow.test {
+            assertTrue(
+                awaitItem().settingRows.contains(Settings.PLAN),
+            )
+        }
+    }
+
     private fun createViewModel(isPreAuth: Boolean = false) = SettingsViewModel(
         firstTimeActionManager = firstTimeManager,
         specialCircumstanceManager = specialCircumstanceManager,
-        environmentRepository = environmentRepository,
         premiumStateManager = premiumStateManager,
         savedStateHandle = SavedStateHandle().apply {
             every { toSettingsArgs() } returns SettingsArgs(isPreAuth = isPreAuth)
diff --git a/core/src/main/kotlin/com/bitwarden/core/data/manager/model/FlagKey.kt b/core/src/main/kotlin/com/bitwarden/core/data/manager/model/FlagKey.kt
index 7f1ae34b90..1b496f9937 100644
--- a/core/src/main/kotlin/com/bitwarden/core/data/manager/model/FlagKey.kt
+++ b/core/src/main/kotlin/com/bitwarden/core/data/manager/model/FlagKey.kt
@@ -45,6 +45,7 @@ sealed class FlagKey<out T : Any> {
                 V2EncryptionPassword,
                 V2EncryptionTde,
                 NewItemTypes,
+                DebugDisableSelfHostPremiumCheck,
             )
         }
     }
@@ -180,6 +181,16 @@ sealed class FlagKey<out T : Any> {
         override val defaultValue: Boolean = false
     }
 
+    /**
+     * Debug-only flag that, when enabled, makes self-hosted environments behave as cloud
+     * environments for premium-upgrade gating. Used by QA to test the premium upgrade flow
+     * against internal self-hosted environments.
+     */
+    data object DebugDisableSelfHostPremiumCheck : FlagKey<Boolean>() {
+        override val keyName: String = "debug-disable-self-host-premium-check"
+        override val defaultValue: Boolean = false
+    }
+
     //region Dummy keys for testing
     /**
      * Data object holding the key for a [Boolean] flag to be used in tests.
diff --git a/ui/src/main/kotlin/com/bitwarden/ui/platform/components/debug/FeatureFlagListItems.kt b/ui/src/main/kotlin/com/bitwarden/ui/platform/components/debug/FeatureFlagListItems.kt
index 003f2ae9e8..1e536f477f 100644
--- a/ui/src/main/kotlin/com/bitwarden/ui/platform/components/debug/FeatureFlagListItems.kt
+++ b/ui/src/main/kotlin/com/bitwarden/ui/platform/components/debug/FeatureFlagListItems.kt
@@ -39,6 +39,7 @@ fun <T : Any> FlagKey<T>.ListItemContent(
     FlagKey.V2EncryptionPassword,
     FlagKey.V2EncryptionTde,
     FlagKey.NewItemTypes,
+    FlagKey.DebugDisableSelfHostPremiumCheck,
         -> {
         @Suppress("UNCHECKED_CAST")
         BooleanFlagItem(
@@ -99,4 +100,7 @@ private fun <T : Any> FlagKey<T>.getDisplayLabel(): String = when (this) {
     FlagKey.V2EncryptionPassword -> stringResource(BitwardenString.v2_encryption_password)
     FlagKey.V2EncryptionTde -> stringResource(BitwardenString.v2_encryption_tde)
     FlagKey.NewItemTypes -> stringResource(BitwardenString.new_item_types)
+    FlagKey.DebugDisableSelfHostPremiumCheck -> {
+        stringResource(BitwardenString.debug_disable_self_host_premium_check)
+    }
 }
diff --git a/ui/src/main/res/values/strings_non_localized.xml b/ui/src/main/res/values/strings_non_localized.xml
index 61a386ec9d..dabe4891c8 100644
--- a/ui/src/main/res/values/strings_non_localized.xml
+++ b/ui/src/main/res/values/strings_non_localized.xml
@@ -53,6 +53,7 @@
     <string name="v2_encryption_password">V2 Encryption - Password</string>
     <string name="manage_devices">Manage devices</string>
     <string name="new_item_types">New Item Types</string>
+    <string name="debug_disable_self_host_premium_check">Debug: Disable self-host premium check</string>
 
     <!-- endregion Debug Menu -->
 </resources>