diff --git a/apps/dev-tool/app/variables/components/app-environment-variables-manager.tsx b/apps/dev-tool/app/variables/components/app-environment-variables-manager.tsx
index 9f58a7d55..1c635a0d8 100644
--- a/apps/dev-tool/app/variables/components/app-environment-variables-manager.tsx
+++ b/apps/dev-tool/app/variables/components/app-environment-variables-manager.tsx
@@ -1,6 +1,6 @@
 'use client';
 
-import { Fragment, useState } from 'react';
+import { Fragment, useCallback, useState } from 'react';
 
 import { useRouter, useSearchParams } from 'next/navigation';
 
@@ -13,6 +13,7 @@ import {
   Copy,
   Eye,
   EyeOff,
+  EyeOffIcon,
   InfoIcon,
 } from 'lucide-react';
 
@@ -39,6 +40,15 @@ import { cn } from '@kit/ui/utils';
 
 import { AppEnvState, EnvVariableState } from '../lib/types';
 
+type ValidationResult = {
+  success: boolean;
+  error?: {
+    issues: Array<{ message: string }>;
+  };
+};
+
+type VariableRecord = Record<string, string>;
+
 export function AppEnvironmentVariablesManager({
   state,
 }: React.PropsWithChildren<{
@@ -97,36 +107,149 @@ function EnvList({ appState }: { appState: AppEnvState }) {
     return value || '(empty)';
   };
 
+  const allVariables = getEffectiveVariablesValue(appState);
+
+  // Create a map of all variables including missing ones that have contextual validation
+  const allVarsWithValidation = envVariables.reduce<
+    Record<string, EnvVariableState>
+  >((acc, model) => {
+    // If the variable exists in appState, use that
+    const existingVar = appState.variables[model.name];
+    if (existingVar) {
+      acc[model.name] = existingVar;
+    } else if (
+      // Show missing variables if they:
+      model.required || // Are marked as required
+      model.contextualValidation // OR have contextual validation
+    ) {
+      // If it doesn't exist but is required or has contextual validation, create an empty state
+      acc[model.name] = {
+        key: model.name,
+        effectiveValue: '',
+        effectiveSource: 'MISSING',
+        category: model.category,
+        isOverridden: false,
+        definitions: [],
+      };
+    }
+    return acc;
+  }, {});
+
   const renderVariable = (varState: EnvVariableState) => {
     const isExpanded = expandedVars[varState.key] ?? false;
     const isClientBundledValue = varState.key.startsWith('NEXT_PUBLIC_');
-
-    // public variables are always visible
     const isValueVisible = showValues[varState.key] ?? isClientBundledValue;
 
-    // grab model is it's a kit variable
     const model = envVariables.find(
       (variable) => variable.name === varState.key,
     );
 
-    const allVariables = Object.values(appState.variables).reduce(
-      (acc, variable) => ({
-        ...acc,
-        [variable.key]: variable.effectiveValue,
-      }),
-      {},
-    );
+    // Enhanced validation logic to handle both regular and contextual validation
+    let validation: ValidationResult = {
+      success: true,
+    };
 
-    const validation = model?.validate
-      ? model.validate({
+    if (model) {
+      // First check if it's required but missing
+      if (model.required && !varState.effectiveValue) {
+        validation = {
+          success: false,
+          error: {
+            issues: [
+              {
+                message: `This variable is required but missing from your environment files`,
+              },
+            ],
+          },
+        };
+      } else if (model.contextualValidation) {
+        // Then check contextual validation
+        const dependenciesMet = model.contextualValidation.dependencies.some(
+          (dep) => {
+            const dependencyValue = allVariables[dep.variable] ?? '';
+
+            return dep.condition(dependencyValue, allVariables);
+          },
+        );
+
+        if (dependenciesMet) {
+          // Only check for missing value or run validation if dependencies are met
+          if (!varState.effectiveValue) {
+            const dependencyErrors = model.contextualValidation.dependencies
+              .map((dep) => {
+                const dependencyValue = allVariables[dep.variable] ?? '';
+
+                const shouldValidate = dep.condition(
+                  dependencyValue,
+                  allVariables,
+                );
+
+                if (shouldValidate) {
+                  const { success } = model.contextualValidation!.validate({
+                    value: varState.effectiveValue,
+                    variables: allVariables,
+                    mode: appState.mode,
+                  });
+
+                  if (success) {
+                    return null;
+                  }
+
+                  return dep.message;
+                }
+
+                return null;
+              })
+              .filter((message): message is string => message !== null);
+
+            validation = {
+              success: dependencyErrors.length === 0,
+              error: {
+                issues: dependencyErrors.map((message) => ({ message })),
+              },
+            };
+          } else {
+            // If we have a value and dependencies are met, run contextual validation
+            const result = model.contextualValidation.validate({
+              value: varState.effectiveValue,
+              variables: allVariables,
+              mode: appState.mode,
+            });
+
+            if (!result.success) {
+              validation = {
+                success: false,
+                error: {
+                  issues: result.error.issues.map((issue) => ({
+                    message: issue.message,
+                  })),
+                },
+              };
+            }
+          }
+        }
+      } else if (model.validate && varState.effectiveValue) {
+        // Only run regular validation if:
+        // 1. There's no contextual validation
+        // 2. There's a value to validate
+        const result = model.validate({
           value: varState.effectiveValue,
           variables: allVariables,
           mode: appState.mode,
-        })
-      : {
-          success: true,
-          error: undefined,
-        };
+        });
+
+        if (!result.success) {
+          validation = {
+            success: false,
+            error: {
+              issues: result.error.issues.map((issue) => ({
+                message: issue.message,
+              })),
+            },
+          };
+        }
+      }
+    }
 
     const canExpand = varState.definitions.length > 1 || !validation.success;
 
@@ -134,12 +257,46 @@ function EnvList({ appState }: { appState: AppEnvState }) {
       <div key={varState.key} className="animate-in fade-in rounded-lg border">
         <div className="p-4">
           <div className="flex items-start justify-between">
-            <div className="flex-1 flex-col gap-y-1">
-              <div className="flex items-center gap-2">
+            <div className="flex-1 flex-col gap-y-4">
+              <div className="flex items-center gap-4">
                 <span className="font-mono text-sm font-semibold">
                   {varState.key}
                 </span>
 
+                {model?.required && <Badge variant="outline">Required</Badge>}
+
+                {varState.effectiveSource === 'MISSING' && (
+                  <Badge
+                    variant={
+                      // Show destructive if required OR if contextual validation dependencies are not met
+                      model?.required ||
+                      model?.contextualValidation?.dependencies.some((dep) => {
+                        const dependencyValue =
+                          allVariables[dep.variable] ?? '';
+
+                        const shouldValidate = dep.condition(
+                          dependencyValue,
+                          allVariables,
+                        );
+
+                        if (!shouldValidate) {
+                          return false;
+                        }
+
+                        return !model.contextualValidation!.validate({
+                          value: varState.effectiveValue,
+                          variables: allVariables,
+                          mode: appState.mode,
+                        }).success;
+                      })
+                        ? 'destructive'
+                        : 'outline'
+                    }
+                  >
+                    Missing
+                  </Badge>
+                )}
+
                 {varState.isOverridden && (
                   <Badge variant="warning">Overridden</Badge>
                 )}
@@ -147,7 +304,7 @@ function EnvList({ appState }: { appState: AppEnvState }) {
 
               <If condition={model}>
                 {(model) => (
-                  <div className="flex items-center gap-2">
+                  <div className="flex items-center gap-2 py-1">
                     <span className="text-muted-foreground text-xs font-normal">
                       {model.description}
                     </span>
@@ -238,33 +395,35 @@ function EnvList({ appState }: { appState: AppEnvState }) {
               </Badge>
             </If>
 
-            <Badge
-              variant={'outline'}
-              className={cn({
-                'text-destructive':
-                  varState.effectiveSource === '.env.production',
-              })}
-            >
-              {varState.effectiveSource}
+            <If condition={varState.effectiveSource !== 'MISSING'}>
+              <Badge
+                variant={'outline'}
+                className={cn({
+                  'text-destructive':
+                    varState.effectiveSource === '.env.production',
+                })}
+              >
+                {varState.effectiveSource}
 
-              <TooltipProvider>
-                <Tooltip>
-                  <TooltipTrigger>
-                    <InfoIcon className="ml-2 h-3 w-3" />
-                  </TooltipTrigger>
+                <TooltipProvider>
+                  <Tooltip>
+                    <TooltipTrigger>
+                      <InfoIcon className="ml-2 h-3 w-3" />
+                    </TooltipTrigger>
 
-                  <TooltipContent>
-                    {varState.effectiveSource === '.env.local'
-                      ? `These variables are specific to this machine and are not committed`
-                      : varState.effectiveSource === '.env.development'
-                        ? `These variables are only being used during development`
-                        : varState.effectiveSource === '.env'
-                          ? `These variables are shared under all modes`
-                          : `These variables are only used in production mode`}
-                  </TooltipContent>
-                </Tooltip>
-              </TooltipProvider>
-            </Badge>
+                    <TooltipContent>
+                      {varState.effectiveSource === '.env.local'
+                        ? `These variables are specific to this machine and are not committed`
+                        : varState.effectiveSource === '.env.development'
+                          ? `These variables are only being used during development`
+                          : varState.effectiveSource === '.env'
+                            ? `These variables are shared under all modes`
+                            : `These variables are only used in production mode`}
+                    </TooltipContent>
+                  </Tooltip>
+                </TooltipProvider>
+              </Badge>
+            </If>
 
             <If condition={varState.isOverridden}>
               <Badge variant="warning">
@@ -313,13 +472,45 @@ function EnvList({ appState }: { appState: AppEnvState }) {
                 </Heading>
 
                 <Alert variant="destructive">
-                  <AlertTitle>Invalid Value</AlertTitle>
+                  <AlertTitle>
+                    {varState.effectiveSource === 'MISSING'
+                      ? 'Missing Required Variable'
+                      : 'Invalid Value'}
+                  </AlertTitle>
 
                   <AlertDescription>
-                    The value for {varState.key} is invalid:
-                    <pre>
-                      <code>{JSON.stringify(validation, null, 2)}</code>
-                    </pre>
+                    <div className="space-y-2">
+                      <div>
+                        {varState.effectiveSource === 'MISSING'
+                          ? `The variable ${varState.key} is required but missing from your environment files:`
+                          : `The value for ${varState.key} is invalid:`}
+                      </div>
+
+                      {/* Enhanced error display */}
+                      <div className="space-y-1">
+                        {validation.error?.issues.map((issue, index) => (
+                          <div key={index} className="text-sm">
+                            • {issue.message}
+                          </div>
+                        ))}
+                      </div>
+
+                      {/* Display dependency information if available */}
+                      {model?.contextualValidation?.dependencies && (
+                        <div className="mt-4 space-y-1">
+                          <div className="font-medium">Dependencies:</div>
+
+                          {model.contextualValidation.dependencies.map(
+                            (dep, index) => (
+                              <div key={index} className="text-sm">
+                                • Requires valid {dep.variable.toUpperCase()}{' '}
+                                when {dep.message}
+                              </div>
+                            ),
+                          )}
+                        </div>
+                      )}
+                    </div>
                   </AlertDescription>
                 </Alert>
               </div>
@@ -401,30 +592,63 @@ function EnvList({ appState }: { appState: AppEnvState }) {
     }
 
     if (invalidVars) {
-      const allVariables = Object.values(appState.variables).reduce(
-        (acc, variable) => ({
-          ...acc,
-          [variable.key]: variable.effectiveValue,
-        }),
-        {},
-      );
+      const allVariables = getEffectiveVariablesValue(appState);
 
-      const hasError =
-        model && model.validate
-          ? !model.validate({
-              value: varState.effectiveValue,
-              variables: allVariables,
-              mode: appState.mode,
-            }).success
-          : false;
+      let hasError = false;
+
+      if (model) {
+        if (model.contextualValidation) {
+          // Check for missing or invalid dependencies
+          const dependencyErrors = model.contextualValidation.dependencies
+            .map((dep) => {
+              const dependencyValue = allVariables[dep.variable] ?? '';
+
+              const shouldValidate = dep.condition(
+                dependencyValue,
+                allVariables,
+              );
+
+              if (shouldValidate) {
+                const { error } = model.contextualValidation!.validate({
+                  value: varState.effectiveValue,
+                  variables: allVariables,
+                  mode: appState.mode,
+                });
+
+                return error;
+              }
+
+              return false;
+            })
+            .filter(Boolean);
+
+          if (dependencyErrors.length > 0) {
+            hasError = true;
+          }
+        } else if (model.validate) {
+          // Fall back to regular validation
+          const result = model.validate({
+            value: varState.effectiveValue,
+            variables: allVariables,
+            mode: appState.mode,
+          });
+
+          hasError = !result.success;
+        }
+      }
 
       if (hasError && isInSearch) return true;
     }
 
+    if (isInSearch) {
+      return true;
+    }
+
     return false;
   };
 
-  const groups = Object.values(appState.variables)
+  // Update groups to use allVarsWithValidation instead of appState.variables
+  const groups = Object.values(allVarsWithValidation)
     .filter(filterVariable)
     .reduce(
       (acc, variable) => {
@@ -445,7 +669,7 @@ function EnvList({ appState }: { appState: AppEnvState }) {
     );
 
   return (
-    <div className="flex flex-col gap-y-8">
+    <div className="flex flex-col gap-y-4">
       <div className="flex items-center">
         <div className="flex w-full space-x-2">
           <div>
@@ -501,7 +725,7 @@ function EnvList({ appState }: { appState: AppEnvState }) {
         </div>
       </div>
 
-      <div className="flex flex-col gap-1">
+      <div className="flex flex-col">
         <Summary appState={appState} />
 
         {groups.map((group) => (
@@ -561,34 +785,13 @@ function FilterSwitcher(props: {
     invalid: boolean;
   };
 }) {
-  const router = useRouter();
-
   const secretVars = props.filters.secret;
   const publicVars = props.filters.public;
   const overriddenVars = props.filters.overridden;
   const privateVars = props.filters.private;
   const invalidVars = props.filters.invalid;
 
-  const handleFilterChange = (key: string, value: boolean) => {
-    const searchParams = new URLSearchParams(window.location.search);
-    const path = window.location.pathname;
-
-    if (key === 'all' && value) {
-      searchParams.delete('secret');
-      searchParams.delete('public');
-      searchParams.delete('overridden');
-      searchParams.delete('private');
-      searchParams.delete('invalid');
-    } else {
-      if (!value) {
-        searchParams.delete(key);
-      } else {
-        searchParams.set(key, 'true');
-      }
-    }
-
-    router.push(`${path}?${searchParams.toString()}`);
-  };
+  const handleFilterChange = useUpdateFilteredVariables();
 
   const buttonLabel = () => {
     const filters = [];
@@ -678,44 +881,155 @@ function FilterSwitcher(props: {
 
 function Summary({ appState }: { appState: AppEnvState }) {
   const varsArray = Object.values(appState.variables);
+  const allVariables = getEffectiveVariablesValue(appState);
   const overridden = varsArray.filter((variable) => variable.isOverridden);
+  const handleFilterChange = useUpdateFilteredVariables();
 
-  const allVariables = varsArray.reduce(
+  // Find all variables with errors (including missing required and contextual validation)
+  const errors = envVariables.reduce<string[]>((acc, model) => {
+    // Get the current value of this variable
+    const varState = appState.variables[model.name];
+    const value = varState?.effectiveValue;
+    let hasError = false;
+
+    // Check if it's required but missing
+    if (model.required && !value) {
+      hasError = true;
+    } else if (model.contextualValidation) {
+      // Check if any dependency conditions are met
+      const dependenciesErrors = model.contextualValidation.dependencies.some(
+        (dep) => {
+          const dependencyValue = allVariables[dep.variable] ?? '';
+
+          const shouldValidate = dep.condition(dependencyValue, allVariables);
+
+          if (shouldValidate) {
+            const { error } = model.contextualValidation!.validate({
+              value: varState?.effectiveValue ?? '',
+              variables: allVariables,
+              mode: appState.mode,
+            });
+
+            return error;
+          }
+        },
+      );
+
+      if (dependenciesErrors) {
+        hasError = true;
+      }
+    } else if (model.validate && value) {
+      // Only run regular validation if:
+      // 1. There's no contextual validation
+      // 2. There's a value to validate
+      const result = model.validate({
+        value,
+        variables: allVariables,
+        mode: appState.mode,
+      });
+
+      if (!result.success) {
+        hasError = true;
+      }
+    }
+
+    if (hasError) {
+      acc.push(model.name);
+    }
+
+    return acc;
+  }, []);
+
+  const validVariables = varsArray.length - errors.length;
+
+  return (
+    <div className="flex justify-between space-x-4">
+      <div className="flex items-center gap-x-2">
+        <Badge variant={'outline'} className={'text-green-500'}>
+          {validVariables} Valid
+        </Badge>
+
+        <Badge
+          variant={'outline'}
+          className={cn({
+            'text-destructive': errors.length > 0,
+            'text-green-500': errors.length === 0,
+          })}
+        >
+          {errors.length} Invalid
+        </Badge>
+
+        <If condition={overridden.length > 0}>
+          <Badge
+            variant={'outline'}
+            className={cn({ 'text-orange-500': overridden.length > 0 })}
+          >
+            {overridden.length} Overridden
+          </Badge>
+        </If>
+      </div>
+
+      <div>
+        <If condition={errors.length > 0}>
+          <Button
+            size={'sm'}
+            variant={'ghost'}
+            onClick={() => handleFilterChange('invalid', true, true)}
+          >
+            <EyeOffIcon className="mr-2 h-3 w-3" />
+            Display Invalid only
+          </Button>
+        </If>
+      </div>
+    </div>
+  );
+}
+
+function getEffectiveVariablesValue(
+  appState: AppEnvState,
+): Record<string, string> {
+  const varsArray = Object.values(appState.variables);
+
+  return varsArray.reduce(
     (acc, variable) => ({
       ...acc,
       [variable.key]: variable.effectiveValue,
     }),
     {},
   );
-
-  const errors = varsArray.filter((variable) => {
-    const model = envVariables.find((v) => variable.key === v.name);
-
-    const validation =
-      model && model.validate
-        ? model.validate({
-            value: variable.effectiveValue,
-            variables: allVariables,
-            mode: appState.mode,
-          })
-        : {
-            success: true,
-          };
-
-    return !validation.success;
-  });
-
-  return (
-    <div className="flex flex-col space-y-4">
-      <div className="flex items-center gap-x-2">
-        <Badge variant={errors.length === 0 ? 'success' : 'destructive'}>
-          {errors.length} Errors
-        </Badge>
-
-        <Badge variant={overridden.length === 0 ? 'success' : 'warning'}>
-          {overridden.length} Overridden Variables
-        </Badge>
-      </div>
-    </div>
-  );
+}
+
+function useUpdateFilteredVariables() {
+  const router = useRouter();
+
+  const handleFilterChange = (key: string, value: boolean, reset = false) => {
+    const searchParams = new URLSearchParams(window.location.search);
+    const path = window.location.pathname;
+
+    const resetAll = () => {
+      searchParams.delete('secret');
+      searchParams.delete('public');
+      searchParams.delete('overridden');
+      searchParams.delete('private');
+      searchParams.delete('invalid');
+    };
+
+    if (reset) {
+      resetAll();
+    }
+
+    if (key === 'all' && value) {
+      resetAll();
+    } else {
+      if (!value) {
+        searchParams.delete(key);
+      } else {
+        searchParams.set(key, 'true');
+      }
+    }
+
+    router.push(`${path}?${searchParams.toString()}`);
+  };
+
+  return useCallback(handleFilterChange, [router]);
 }
diff --git a/apps/dev-tool/app/variables/lib/env-scanner.ts b/apps/dev-tool/app/variables/lib/env-scanner.ts
index 59a387397..e1c164998 100644
--- a/apps/dev-tool/app/variables/lib/env-scanner.ts
+++ b/apps/dev-tool/app/variables/lib/env-scanner.ts
@@ -1,9 +1,9 @@
 import 'server-only';
 
-import { envVariables } from '@/app/variables/lib/env-variables-model';
 import fs from 'fs/promises';
 import path from 'path';
 
+import { envVariables } from './env-variables-model';
 import {
   AppEnvState,
   EnvFileInfo,
diff --git a/apps/dev-tool/app/variables/lib/env-variables-model.ts b/apps/dev-tool/app/variables/lib/env-variables-model.ts
index b5537f47b..677d61120 100644
--- a/apps/dev-tool/app/variables/lib/env-variables-model.ts
+++ b/apps/dev-tool/app/variables/lib/env-variables-model.ts
@@ -1,10 +1,26 @@
 import { EnvMode } from '@/app/variables/lib/types';
 import { z } from 'zod';
 
+type DependencyRule = {
+  variable: string;
+  condition: (value: string, variables: Record<string, string>) => boolean;
+  message: string;
+};
+
+type ContextualValidation = {
+  dependencies: DependencyRule[];
+  validate: (props: {
+    value: string;
+    variables: Record<string, string>;
+    mode: EnvMode;
+  }) => z.SafeParseReturnType<unknown, unknown>;
+};
+
 export type EnvVariableModel = {
   name: string;
   description: string;
   secret?: boolean;
+  required?: boolean;
   category: string;
   test?: (value: string) => Promise<boolean>;
   validate?: (props: {
@@ -12,6 +28,7 @@ export type EnvVariableModel = {
     variables: Record<string, string>;
     mode: EnvMode;
   }) => z.SafeParseReturnType<unknown, unknown>;
+  contextualValidation?: ContextualValidation;
 };
 
 export const envVariables: EnvVariableModel[] = [
@@ -20,6 +37,7 @@ export const envVariables: EnvVariableModel[] = [
     description:
       'The URL of your site, used for generating absolute URLs. Must include the protocol.',
     category: 'Site Configuration',
+    required: true,
     validate: ({ value, mode }) => {
       if (mode === 'development') {
         return z
@@ -47,6 +65,7 @@ export const envVariables: EnvVariableModel[] = [
     description:
       "Your product's name, used consistently across the application interface.",
     category: 'Site Configuration',
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -62,6 +81,7 @@ export const envVariables: EnvVariableModel[] = [
     description:
       "The site's title tag content, crucial for SEO and browser display.",
     category: 'Site Configuration',
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -77,6 +97,7 @@ export const envVariables: EnvVariableModel[] = [
     description:
       "Your site's meta description, important for SEO optimization.",
     category: 'Site Configuration',
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -133,6 +154,27 @@ export const envVariables: EnvVariableModel[] = [
       'Your Cloudflare Captcha secret token for backend verification.',
     category: 'Security',
     secret: true,
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'NEXT_PUBLIC_CAPTCHA_SITE_KEY',
+          condition: (value) => {
+            return value !== '';
+          },
+          message:
+            'CAPTCHA_SECRET_TOKEN is required when NEXT_PUBLIC_CAPTCHA_SITE_KEY is set',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The CAPTCHA_SECRET_TOKEN variable must be at least 1 character`,
+          )
+          .safeParse(value);
+      },
+    },
     validate: ({ value }) => {
       return z
         .string()
@@ -286,6 +328,7 @@ export const envVariables: EnvVariableModel[] = [
     name: 'NEXT_PUBLIC_SUPABASE_URL',
     description: 'Your Supabase project URL.',
     category: 'Supabase',
+    required: true,
     validate: ({ value, mode }) => {
       if (mode === 'development') {
         return z
@@ -312,6 +355,7 @@ export const envVariables: EnvVariableModel[] = [
     name: 'NEXT_PUBLIC_SUPABASE_ANON_KEY',
     description: 'Your Supabase anonymous API key.',
     category: 'Supabase',
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -319,7 +363,6 @@ export const envVariables: EnvVariableModel[] = [
           1,
           `The NEXT_PUBLIC_SUPABASE_ANON_KEY variable must be at least 1 character`,
         )
-        .optional()
         .safeParse(value);
     },
   },
@@ -328,6 +371,7 @@ export const envVariables: EnvVariableModel[] = [
     description: 'Your Supabase service role key (keep this secret!).',
     category: 'Supabase',
     secret: true,
+    required: true,
     validate: ({ value, variables }) => {
       return z
         .string()
@@ -335,7 +379,6 @@ export const envVariables: EnvVariableModel[] = [
           1,
           `The SUPABASE_SERVICE_ROLE_KEY variable must be at least 1 character`,
         )
-        .optional()
         .refine(
           (value) => {
             return value !== variables['NEXT_PUBLIC_SUPABASE_ANON_KEY'];
@@ -352,6 +395,7 @@ export const envVariables: EnvVariableModel[] = [
     description: 'Secret key for Supabase webhook verification.',
     category: 'Supabase',
     secret: true,
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -368,6 +412,7 @@ export const envVariables: EnvVariableModel[] = [
     description:
       'Your chosen billing provider. Options: stripe or lemon-squeezy.',
     category: 'Billing',
+    required: true,
     validate: ({ value }) => {
       return z.enum(['stripe', 'lemon-squeezy']).optional().safeParse(value);
     },
@@ -376,6 +421,33 @@ export const envVariables: EnvVariableModel[] = [
     name: 'NEXT_PUBLIC_STRIPE_PUBLISHABLE_KEY',
     description: 'Your Stripe publishable key.',
     category: 'Billing',
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'NEXT_PUBLIC_BILLING_PROVIDER',
+          condition: (value) => value === 'stripe',
+          message:
+            'NEXT_PUBLIC_STRIPE_PUBLISHABLE_KEY is required when NEXT_PUBLIC_BILLING_PROVIDER is set to "stripe"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The NEXT_PUBLIC_STRIPE_PUBLISHABLE_KEY variable must be at least 1 character`,
+          )
+          .refine(
+            (value) => {
+              return value.startsWith('pk_');
+            },
+            {
+              message: `The NEXT_PUBLIC_STRIPE_PUBLISHABLE_KEY variable must start with pk_`,
+            },
+          )
+          .safeParse(value);
+      },
+    },
     validate: ({ value }) => {
       return z
         .string()
@@ -392,6 +464,30 @@ export const envVariables: EnvVariableModel[] = [
     description: 'Your Stripe secret key.',
     category: 'Billing',
     secret: true,
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'NEXT_PUBLIC_BILLING_PROVIDER',
+          condition: (value) => value === 'stripe',
+          message:
+            'STRIPE_SECRET_KEY is required when NEXT_PUBLIC_BILLING_PROVIDER is set to "stripe"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(1, `The STRIPE_SECRET_KEY variable must be at least 1 character`)
+          .refine(
+            (value) => {
+              return value.startsWith('sk_') || value.startsWith('rk_');
+            },
+            {
+              message: `The STRIPE_SECRET_KEY variable must start with sk_ or rk_`,
+            },
+          )
+          .safeParse(value);
+      },
+    },
     validate: ({ value }) => {
       return z
         .string()
@@ -405,6 +501,33 @@ export const envVariables: EnvVariableModel[] = [
     description: 'Your Stripe webhook secret.',
     category: 'Billing',
     secret: true,
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'NEXT_PUBLIC_BILLING_PROVIDER',
+          condition: (value) => value === 'stripe',
+          message:
+            'STRIPE_WEBHOOK_SECRET is required when NEXT_PUBLIC_BILLING_PROVIDER is set to "stripe"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The STRIPE_WEBHOOK_SECRET variable must be at least 1 character`,
+          )
+          .refine(
+            (value) => {
+              return value.startsWith('whsec_');
+            },
+            {
+              message: `The STRIPE_WEBHOOK_SECRET variable must start with whsec_`,
+            },
+          )
+          .safeParse(value);
+      },
+    },
     validate: ({ value }) => {
       return z
         .string()
@@ -421,6 +544,25 @@ export const envVariables: EnvVariableModel[] = [
     description: 'Your Lemon Squeezy secret key.',
     category: 'Billing',
     secret: true,
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'NEXT_PUBLIC_BILLING_PROVIDER',
+          condition: (value) => value === 'lemon-squeezy',
+          message:
+            'LEMON_SQUEEZY_SECRET_KEY is required when NEXT_PUBLIC_BILLING_PROVIDER is set to "lemon-squeezy"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The LEMON_SQUEEZY_SECRET_KEY variable must be at least 1 character`,
+          )
+          .safeParse(value);
+      },
+    },
     validate: ({ value }) => {
       return z
         .string()
@@ -436,6 +578,25 @@ export const envVariables: EnvVariableModel[] = [
     name: 'LEMON_SQUEEZY_STORE_ID',
     description: 'Your Lemon Squeezy store ID.',
     category: 'Billing',
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'NEXT_PUBLIC_BILLING_PROVIDER',
+          condition: (value) => value === 'lemon-squeezy',
+          message:
+            'LEMON_SQUEEZY_STORE_ID is required when NEXT_PUBLIC_BILLING_PROVIDER is set to "lemon-squeezy"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The LEMON_SQUEEZY_STORE_ID variable must be at least 1 character`,
+          )
+          .safeParse(value);
+      },
+    },
     validate: ({ value }) => {
       return z
         .string()
@@ -452,6 +613,25 @@ export const envVariables: EnvVariableModel[] = [
     description: 'Your Lemon Squeezy signing secret.',
     category: 'Billing',
     secret: true,
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'NEXT_PUBLIC_BILLING_PROVIDER',
+          condition: (value) => value === 'lemon-squeezy',
+          message:
+            'LEMON_SQUEEZY_SIGNING_SECRET is required when NEXT_PUBLIC_BILLING_PROVIDER is set to "lemon-squeezy"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The LEMON_SQUEEZY_SIGNING_SECRET variable must be at least 1 character`,
+          )
+          .safeParse(value);
+      },
+    },
     validate: ({ value }) => {
       return z
         .string()
@@ -467,14 +647,16 @@ export const envVariables: EnvVariableModel[] = [
     name: 'MAILER_PROVIDER',
     description: 'Your email service provider. Options: nodemailer or resend.',
     category: 'Email',
+    required: true,
     validate: ({ value }) => {
-      return z.enum(['nodemailer', 'resend']).optional().safeParse(value);
+      return z.enum(['nodemailer', 'resend']).safeParse(value);
     },
   },
   {
     name: 'EMAIL_SENDER',
     description: 'Default sender email address.',
     category: 'Email',
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -486,6 +668,7 @@ export const envVariables: EnvVariableModel[] = [
     name: 'CONTACT_EMAIL',
     description: 'Email address for contact form submissions.',
     category: 'Email',
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -499,42 +682,99 @@ export const envVariables: EnvVariableModel[] = [
     description: 'Your Resend API key.',
     category: 'Email',
     secret: true,
-    validate: ({ value }) => {
-      return z
-        .string()
-        .min(1, `The RESEND_API_KEY variable must be at least 1 character`)
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'MAILER_PROVIDER',
+          condition: (value) => value === 'resend',
+          message:
+            'RESEND_API_KEY is required when MAILER_PROVIDER is set to "resend"',
+        },
+      ],
+      validate: ({ value, variables }) => {
+        if (variables['MAILER_PROVIDER'] === 'resend') {
+          return z
+            .string()
+            .min(1, `The RESEND_API_KEY variable must be at least 1 character`)
+            .safeParse(value);
+        }
+
+        return z.string().optional().safeParse(value);
+      },
     },
   },
   {
     name: 'EMAIL_HOST',
     description: 'SMTP host for Nodemailer configuration.',
     category: 'Email',
-    validate: ({ value }) => {
-      return z.string().safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'MAILER_PROVIDER',
+          condition: (value) => value === 'nodemailer',
+          message:
+            'EMAIL_HOST is required when MAILER_PROVIDER is set to "nodemailer"',
+        },
+      ],
+      validate: ({ value, variables }) => {
+        if (variables['MAILER_PROVIDER'] === 'nodemailer') {
+          return z
+            .string()
+            .min(1, 'The EMAIL_HOST variable must be at least 1 character')
+            .safeParse(value);
+        }
+        return z.string().optional().safeParse(value);
+      },
     },
   },
   {
     name: 'EMAIL_PORT',
     description: 'SMTP port for Nodemailer configuration.',
     category: 'Email',
-    validate: ({ value }) => {
-      return z.coerce
-        .number()
-        .min(1, `The EMAIL_PORT variable must be at least 1 character`)
-        .max(65535, `The EMAIL_PORT variable must be at most 65535`)
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'MAILER_PROVIDER',
+          condition: (value) => value === 'nodemailer',
+          message:
+            'EMAIL_PORT is required when MAILER_PROVIDER is set to "nodemailer"',
+        },
+      ],
+      validate: ({ value, variables }) => {
+        if (variables['MAILER_PROVIDER'] === 'nodemailer') {
+          return z.coerce
+            .number()
+            .min(1, 'The EMAIL_PORT variable must be at least 1')
+            .max(65535, 'The EMAIL_PORT variable must be at most 65535')
+            .safeParse(value);
+        }
+        return z.coerce.number().optional().safeParse(value);
+      },
     },
   },
   {
     name: 'EMAIL_USER',
     description: 'SMTP user for Nodemailer configuration.',
     category: 'Email',
-    validate: ({ value }) => {
-      return z
-        .string()
-        .min(1, `The EMAIL_USER variable must be at least 1 character`)
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'MAILER_PROVIDER',
+          condition: (value) => value === 'nodemailer',
+          message:
+            'EMAIL_USER is required when MAILER_PROVIDER is set to "nodemailer"',
+        },
+      ],
+      validate: ({ value, variables }) => {
+        if (variables['MAILER_PROVIDER'] === 'nodemailer') {
+          return z
+            .string()
+            .min(1, 'The EMAIL_USER variable must be at least 1 character')
+            .safeParse(value);
+        }
+
+        return z.string().optional().safeParse(value);
+      },
     },
   },
   {
@@ -542,17 +782,46 @@ export const envVariables: EnvVariableModel[] = [
     description: 'SMTP password for Nodemailer configuration.',
     category: 'Email',
     secret: true,
-    validate: ({ value }) => {
-      return z
-        .string()
-        .min(1, `The EMAIL_PASSWORD variable must be at least 1 character`)
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'MAILER_PROVIDER',
+          condition: (value) => value === 'nodemailer',
+          message:
+            'EMAIL_PASSWORD is required when MAILER_PROVIDER is set to "nodemailer"',
+        },
+      ],
+      validate: ({ value, variables }) => {
+        if (variables['MAILER_PROVIDER'] === 'nodemailer') {
+          return z
+            .string()
+            .min(1, 'The EMAIL_PASSWORD variable must be at least 1 character')
+            .safeParse(value);
+        }
+        return z.string().optional().safeParse(value);
+      },
     },
   },
   {
     name: 'EMAIL_TLS',
     description: 'Whether to use TLS for SMTP connection.',
     category: 'Email',
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'MAILER_PROVIDER',
+          condition: (value) => value === 'nodemailer',
+          message:
+            'EMAIL_TLS is required when MAILER_PROVIDER is set to "nodemailer"',
+        },
+      ],
+      validate: ({ value, variables }) => {
+        if (variables['MAILER_PROVIDER'] === 'nodemailer') {
+          return z.coerce.boolean().optional().safeParse(value);
+        }
+        return z.coerce.boolean().optional().safeParse(value);
+      },
+    },
     validate: ({ value }) => {
       return z.coerce.boolean().optional().safeParse(value);
     },
@@ -569,23 +838,50 @@ export const envVariables: EnvVariableModel[] = [
     name: 'NEXT_PUBLIC_KEYSTATIC_STORAGE_KIND',
     description: 'Your Keystatic storage kind. Options: local, cloud, github.',
     category: 'CMS',
-    validate: ({ value }) => {
-      return z.enum(['local', 'cloud', 'github']).optional().safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'CMS_CLIENT',
+          condition: (value) => value === 'keystatic',
+          message:
+            'NEXT_PUBLIC_KEYSTATIC_STORAGE_KIND is required when CMS_CLIENT is set to "keystatic"',
+        },
+      ],
+      validate: ({ value, variables }) => {
+        if (variables['CMS_CLIENT'] === 'keystatic') {
+          return z
+            .enum(['local', 'cloud', 'github'])
+            .optional()
+            .safeParse(value);
+        }
+        return z.enum(['local', 'cloud', 'github']).optional().safeParse(value);
+      },
     },
   },
   {
     name: 'NEXT_PUBLIC_KEYSTATIC_STORAGE_REPO',
     description: 'Your Keystatic storage repo.',
     category: 'CMS',
-    validate: ({ value }) => {
-      return z
-        .string()
-        .min(
-          1,
-          `The NEXT_PUBLIC_KEYSTATIC_STORAGE_REPO variable must be at least 1 character`,
-        )
-        .optional()
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'CMS_CLIENT',
+          condition: (value, variables) =>
+            value === 'keystatic' &&
+            variables['NEXT_PUBLIC_KEYSTATIC_STORAGE_KIND'] === 'github',
+          message:
+            'NEXT_PUBLIC_KEYSTATIC_STORAGE_REPO is required when CMS_CLIENT is set to "keystatic"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The NEXT_PUBLIC_KEYSTATIC_STORAGE_REPO variable must be at least 1 character`,
+          )
+          .safeParse(value);
+      },
     },
   },
   {
@@ -593,58 +889,94 @@ export const envVariables: EnvVariableModel[] = [
     description: 'Your Keystatic GitHub token.',
     category: 'CMS',
     secret: true,
-    validate: ({ value }) => {
-      return z
-        .string()
-        .min(
-          1,
-          `The KEYSTATIC_GITHUB_TOKEN variable must be at least 1 character`,
-        )
-        .optional()
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'CMS_CLIENT',
+          condition: (value, variables) =>
+            value === 'keystatic' &&
+            variables['NEXT_PUBLIC_KEYSTATIC_STORAGE_KIND'] === 'github',
+          message:
+            'KEYSTATIC_GITHUB_TOKEN is required when CMS_CLIENT is set to "keystatic"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The KEYSTATIC_GITHUB_TOKEN variable must be at least 1 character`,
+          )
+          .safeParse(value);
+      },
     },
   },
   {
     name: 'KEYSTATIC_PATH_PREFIX',
     description: 'Your Keystatic path prefix.',
     category: 'CMS',
-    validate: ({ value }) => {
-      return z
-        .string()
-        .min(
-          1,
-          `The KEYSTATIC_PATH_PREFIX variable must be at least 1 character`,
-        )
-        .optional()
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'CMS_CLIENT',
+          condition: (value) => value === 'keystatic',
+          message:
+            'KEYSTATIC_PATH_PREFIX is required when CMS_CLIENT is set to "keystatic"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .safeParse(value);
+      },
     },
   },
   {
     name: 'NEXT_PUBLIC_KEYSTATIC_CONTENT_PATH',
     description: 'Your Keystatic content path.',
     category: 'CMS',
-    validate: ({ value }) => {
-      return z
-        .string()
-        .min(
-          1,
-          `The NEXT_PUBLIC_KEYSTATIC_CONTENT_PATH variable must be at least 1 character`,
-        )
-        .optional()
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'CMS_CLIENT',
+          condition: (value) => value === 'keystatic',
+          message:
+            'NEXT_PUBLIC_KEYSTATIC_CONTENT_PATH is required when CMS_CLIENT is set to "keystatic"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The NEXT_PUBLIC_KEYSTATIC_CONTENT_PATH variable must be at least 1 character`,
+          )
+          .optional()
+          .safeParse(value);
+      },
     },
   },
   {
     name: 'WORDPRESS_API_URL',
     description: 'WordPress API URL when using WordPress as CMS.',
     category: 'CMS',
-    validate: ({ value }) => {
-      return z
-        .string()
-        .url({
-          message: `The WORDPRESS_API_URL variable must be a valid URL`,
-        })
-        .safeParse(value);
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'CMS_CLIENT',
+          condition: (value) => value === 'wordpress',
+          message:
+            'WORDPRESS_API_URL is required when CMS_CLIENT is set to "wordpress"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .url({
+            message: `The WORDPRESS_API_URL variable must be a valid URL`,
+          })
+          .safeParse(value);
+      },
     },
   },
   {
@@ -679,45 +1011,6 @@ export const envVariables: EnvVariableModel[] = [
       return z.coerce.boolean().optional().safeParse(value);
     },
   },
-  {
-    name: `ENABLE_REACT_COMPILER`,
-    description: 'Enables the React compiler [experimental]',
-    category: 'Features',
-    validate: ({ value }) => {
-      return z.coerce.boolean().optional().safeParse(value);
-    },
-  },
-  {
-    name: 'NEXT_PUBLIC_MONITORING_PROVIDER',
-    description: 'The monitoring provider to use.',
-    category: 'Monitoring',
-    validate: ({ value }) => {
-      return z.enum(['baselime', 'sentry']).optional().safeParse(value);
-    },
-  },
-  {
-    name: 'NEXT_PUBLIC_BASELIME_KEY',
-    description: 'The Baselime key to use.',
-    category: 'Monitoring',
-    validate: ({ value }) => {
-      return z
-        .string()
-        .min(
-          1,
-          `The NEXT_PUBLIC_BASELIME_KEY variable must be at least 1 character`,
-        )
-        .optional()
-        .safeParse(value);
-    },
-  },
-  {
-    name: 'STRIPE_ENABLE_TRIAL_WITHOUT_CC',
-    description: 'Enables trial plans without credit card.',
-    category: 'Billing',
-    validate: ({ value }) => {
-      return z.coerce.boolean().optional().safeParse(value);
-    },
-  },
   {
     name: 'NEXT_PUBLIC_VERSION_UPDATER_REFETCH_INTERVAL_SECONDS',
     description: 'The interval in seconds to check for updates.',
@@ -737,10 +1030,61 @@ export const envVariables: EnvVariableModel[] = [
         .safeParse(value);
     },
   },
+  {
+    name: `ENABLE_REACT_COMPILER`,
+    description: 'Enables the React compiler [experimental]',
+    category: 'Build',
+    validate: ({ value }) => {
+      return z.coerce.boolean().optional().safeParse(value);
+    },
+  },
+  {
+    name: 'NEXT_PUBLIC_MONITORING_PROVIDER',
+    description: 'The monitoring provider to use.',
+    category: 'Monitoring',
+    required: true,
+    validate: ({ value }) => {
+      return z.enum(['baselime', 'sentry', '']).optional().safeParse(value);
+    },
+  },
+  {
+    name: 'NEXT_PUBLIC_BASELIME_KEY',
+    description: 'The Baselime key to use.',
+    category: 'Monitoring',
+    contextualValidation: {
+      dependencies: [
+        {
+          variable: 'NEXT_PUBLIC_MONITORING_PROVIDER',
+          condition: (value) => value === 'baselime',
+          message:
+            'NEXT_PUBLIC_BASELIME_KEY is required when NEXT_PUBLIC_MONITORING_PROVIDER is set to "baselime"',
+        },
+      ],
+      validate: ({ value }) => {
+        return z
+          .string()
+          .min(
+            1,
+            `The NEXT_PUBLIC_BASELIME_KEY variable must be at least 1 character`,
+          )
+          .optional()
+          .safeParse(value);
+      },
+    },
+  },
+  {
+    name: 'STRIPE_ENABLE_TRIAL_WITHOUT_CC',
+    description: 'Enables trial plans without credit card.',
+    category: 'Billing',
+    validate: ({ value }) => {
+      return z.coerce.boolean().optional().safeParse(value);
+    },
+  },
   {
     name: 'NEXT_PUBLIC_THEME_COLOR',
     description: 'The default theme color.',
     category: 'Theme',
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -756,6 +1100,7 @@ export const envVariables: EnvVariableModel[] = [
     name: 'NEXT_PUBLIC_THEME_COLOR_DARK',
     description: 'The default theme color for dark mode.',
     category: 'Theme',
+    required: true,
     validate: ({ value }) => {
       return z
         .string()
@@ -767,4 +1112,12 @@ export const envVariables: EnvVariableModel[] = [
         .safeParse(value);
     },
   },
+  {
+    name: 'NEXT_PUBLIC_DISPLAY_TERMS_AND_CONDITIONS_CHECKBOX',
+    description: 'Whether to display the terms checkbox during sign-up.',
+    category: 'Features',
+    validate: ({ value }) => {
+      return z.coerce.boolean().optional().safeParse(value);
+    },
+  },
 ];
diff --git a/apps/web/middleware.ts b/apps/web/middleware.ts
index fe1ebf677..34b6ec29d 100644
--- a/apps/web/middleware.ts
+++ b/apps/web/middleware.ts
@@ -115,6 +115,18 @@ async function adminMiddleware(request: NextRequest, response: NextResponse) {
     );
   }
 
+  const supabase = createMiddlewareClient(request, response);
+
+  const requiresMultiFactorAuthentication =
+    await checkRequiresMultiFactorAuthentication(supabase);
+
+  // If user requires multi-factor authentication, redirect to MFA page.
+  if (requiresMultiFactorAuthentication) {
+    return NextResponse.redirect(
+      new URL(pathsConfig.auth.verifyMfa, origin).href,
+    );
+  }
+
   const role = user?.app_metadata.role;
 
   // If user is not an admin, redirect to 404 page.
diff --git a/packages/features/admin/src/lib/server/utils/is-super-admin.ts b/packages/features/admin/src/lib/server/utils/is-super-admin.ts
index 1b0deaec1..16b34589d 100644
--- a/packages/features/admin/src/lib/server/utils/is-super-admin.ts
+++ b/packages/features/admin/src/lib/server/utils/is-super-admin.ts
@@ -1,5 +1,6 @@
 import { SupabaseClient } from '@supabase/supabase-js';
 
+import { checkRequiresMultiFactorAuthentication } from '@kit/supabase/check-requires-mfa';
 import { Database } from '@kit/supabase/database';
 
 /**
@@ -18,6 +19,14 @@ export async function isSuperAdmin(client: SupabaseClient<Database>) {
     return false;
   }
 
+  const requiresMultiFactorAuthentication =
+    await checkRequiresMultiFactorAuthentication(client);
+
+  // If user requires multi-factor authentication, deny access.
+  if (requiresMultiFactorAuthentication) {
+    return false;
+  }
+
   const appMetadata = data.user.app_metadata;
 
   return appMetadata?.role === 'super-admin';