diff --git a/waspc/e2e-test/test-outputs/waspBuild-golden/waspBuild/main.wasp b/waspc/e2e-test/test-outputs/waspBuild-golden/waspBuild/main.wasp
index 1f02583e4f..88044a7c03 100644
--- a/waspc/e2e-test/test-outputs/waspBuild-golden/waspBuild/main.wasp
+++ b/waspc/e2e-test/test-outputs/waspBuild-golden/waspBuild/main.wasp
@@ -1,6 +1,6 @@
 app waspBuild {
   wasp: {
-    version: "^0.15.2"
+    version: "^0.16.0"
   },
   title: "waspBuild"
 }
diff --git a/waspc/e2e-test/test-outputs/waspCompile-golden/waspCompile/main.wasp b/waspc/e2e-test/test-outputs/waspCompile-golden/waspCompile/main.wasp
index 982cf4e8f0..70a8f46525 100644
--- a/waspc/e2e-test/test-outputs/waspCompile-golden/waspCompile/main.wasp
+++ b/waspc/e2e-test/test-outputs/waspCompile-golden/waspCompile/main.wasp
@@ -1,6 +1,6 @@
 app waspCompile {
   wasp: {
-    version: "^0.15.2"
+    version: "^0.16.0"
   },
   title: "waspCompile"
 }
diff --git a/waspc/e2e-test/test-outputs/waspComplexTest-golden/waspComplexTest/main.wasp b/waspc/e2e-test/test-outputs/waspComplexTest-golden/waspComplexTest/main.wasp
index dd7184c671..48fddedeec 100644
--- a/waspc/e2e-test/test-outputs/waspComplexTest-golden/waspComplexTest/main.wasp
+++ b/waspc/e2e-test/test-outputs/waspComplexTest-golden/waspComplexTest/main.wasp
@@ -1,6 +1,6 @@
 app waspComplexTest {
   wasp: {
-    version: "^0.15.2"
+    version: "^0.16.0"
   },
   auth: {
     userEntity: User,
diff --git a/waspc/e2e-test/test-outputs/waspJob-golden/waspJob/main.wasp b/waspc/e2e-test/test-outputs/waspJob-golden/waspJob/main.wasp
index 815644889f..f0a485ec43 100644
--- a/waspc/e2e-test/test-outputs/waspJob-golden/waspJob/main.wasp
+++ b/waspc/e2e-test/test-outputs/waspJob-golden/waspJob/main.wasp
@@ -1,6 +1,6 @@
 app waspJob {
   wasp: {
-    version: "^0.15.2"
+    version: "^0.16.0"
   },
   title: "waspJob"
 }
diff --git a/waspc/e2e-test/test-outputs/waspMigrate-golden/waspMigrate/main.wasp b/waspc/e2e-test/test-outputs/waspMigrate-golden/waspMigrate/main.wasp
index 2a6ad7d962..99e0d47b2d 100644
--- a/waspc/e2e-test/test-outputs/waspMigrate-golden/waspMigrate/main.wasp
+++ b/waspc/e2e-test/test-outputs/waspMigrate-golden/waspMigrate/main.wasp
@@ -1,6 +1,6 @@
 app waspMigrate {
   wasp: {
-    version: "^0.15.2"
+    version: "^0.16.0"
   },
   title: "waspMigrate"
 }
diff --git a/waspc/e2e-test/test-outputs/waspNew-golden/waspNew/main.wasp b/waspc/e2e-test/test-outputs/waspNew-golden/waspNew/main.wasp
index 96b3500b7f..995a2401e8 100644
--- a/waspc/e2e-test/test-outputs/waspNew-golden/waspNew/main.wasp
+++ b/waspc/e2e-test/test-outputs/waspNew-golden/waspNew/main.wasp
@@ -1,6 +1,6 @@
 app waspNew {
   wasp: {
-    version: "^0.15.2"
+    version: "^0.16.0"
   },
   title: "waspNew"
 }
diff --git a/waspc/examples/todoApp/main.wasp b/waspc/examples/todoApp/main.wasp
index f827d34e83..9dd232da7d 100644
--- a/waspc/examples/todoApp/main.wasp
+++ b/waspc/examples/todoApp/main.wasp
@@ -1,6 +1,6 @@
 app todoApp {
   wasp: {
-    version: "^0.15.0"
+    version: "^0.16.0"
   },
   title: "ToDo App",
   // head: [],
diff --git a/waspc/examples/todoApp/package-lock.json b/waspc/examples/todoApp/package-lock.json
index 9b072296ec..c834474f40 100644
--- a/waspc/examples/todoApp/package-lock.json
+++ b/waspc/examples/todoApp/package-lock.json
@@ -11,6 +11,7 @@
         "react": "^18.2.0",
         "react-dom": "^18.2.0",
         "react-router-dom": "^6.26.2",
+        "tailwindcss": "^3.2.7",
         "wasp": "file:.wasp/out/sdk/wasp"
       },
       "devDependencies": {
diff --git a/waspc/examples/todoApp/package.json b/waspc/examples/todoApp/package.json
index df4c8fc162..5bb1ee9f41 100644
--- a/waspc/examples/todoApp/package.json
+++ b/waspc/examples/todoApp/package.json
@@ -11,7 +11,8 @@
     "react": "^18.2.0",
     "react-dom": "^18.2.0",
     "react-router-dom": "^6.26.2",
-    "wasp": "file:.wasp/out/sdk/wasp"
+    "wasp": "file:.wasp/out/sdk/wasp",
+    "tailwindcss": "^3.2.7"
   },
   "devDependencies": {
     "@types/express": "^4.17.13",
diff --git a/waspc/headless-test/examples/todoApp/package.json b/waspc/headless-test/examples/todoApp/package.json
index 15751e4481..be070df5b7 100644
--- a/waspc/headless-test/examples/todoApp/package.json
+++ b/waspc/headless-test/examples/todoApp/package.json
@@ -6,7 +6,8 @@
     "react": "^18.2.0",
     "react-dom": "^18.2.0",
     "react-router-dom": "^6.26.2",
-    "wasp": "file:.wasp/out/sdk/wasp"
+    "wasp": "file:.wasp/out/sdk/wasp",
+    "tailwindcss": "^3.2.7"
   },
   "devDependencies": {
     "@types/cors": "^2.8.5",
diff --git a/waspc/src/Wasp/AppSpec.hs b/waspc/src/Wasp/AppSpec.hs
index 44b4196601..adf351bdac 100644
--- a/waspc/src/Wasp/AppSpec.hs
+++ b/waspc/src/Wasp/AppSpec.hs
@@ -16,7 +16,6 @@ module Wasp.AppSpec
     getRoutes,
     getJobs,
     resolveRef,
-    doesConfigFileExist,
     asAbsWaspProjectDirFile,
     getApp,
     getApiNamespaces,
@@ -26,7 +25,7 @@ module Wasp.AppSpec
 where
 
 import Data.List (find)
-import Data.Maybe (fromMaybe, isJust)
+import Data.Maybe (fromMaybe)
 import Data.Text (Text)
 import StrongPath (Abs, Dir, File', Path', Rel, (</>))
 import Wasp.AppSpec.Action (Action)
@@ -149,10 +148,6 @@ resolveRef spec ref =
     $ find ((== refName ref) . fst) $
       getDecls spec
 
-doesConfigFileExist :: AppSpec -> Path' (Rel WaspProjectDir) File' -> Bool
-doesConfigFileExist spec file =
-  isJust $ find ((==) file . _pathInWaspProjectDir) (configFiles spec)
-
 asAbsWaspProjectDirFile :: AppSpec -> Path' (Rel WaspProjectDir) File' -> Path' Abs File'
 asAbsWaspProjectDirFile spec file = waspProjectDir spec </> file
 
diff --git a/waspc/src/Wasp/Generator/ConfigFile.hs b/waspc/src/Wasp/Generator/ConfigFile.hs
index 59cb157810..2e1037af06 100644
--- a/waspc/src/Wasp/Generator/ConfigFile.hs
+++ b/waspc/src/Wasp/Generator/ConfigFile.hs
@@ -4,9 +4,11 @@ module Wasp.Generator.ConfigFile
   )
 where
 
+import Data.List (find)
 import Data.Map (fromList)
+import Data.Maybe (isJust)
 import StrongPath (File', Path', Rel, castRel, relfile, (</>))
-import Wasp.AppSpec (AppSpec, doesConfigFileExist)
+import qualified Wasp.AppSpec.ConfigFile as CF
 import Wasp.ConfigFile (ConfigFileRelocationMap)
 import Wasp.Generator.Common (ProjectRootDir)
 import Wasp.Generator.WebAppGenerator.Common (webAppRootDirInProjectRootDir)
@@ -24,12 +26,16 @@ asProjectRootDirConfigFile = (webAppRootDirInProjectRootDir </>) . castRel
 -- | Helper that determines if Tailwind used. For our purposes, we allow
 -- developers to opt-in by creating both a tailwind config file and
 -- postcss config file in their wasp project dir.
-isTailwindUsed :: AppSpec -> Bool
-isTailwindUsed spec =
-  doesConfigFileExist spec tailwindConfigFile
-    && doesConfigFileExist spec postcssConfigFile
+isTailwindUsed :: [CF.ConfigFileRelocator] -> Bool
+isTailwindUsed configFileRelocators =
+  doesConfigFileExist tailwindConfigFile
+    && doesConfigFileExist postcssConfigFile
+  where
+    doesConfigFileExist :: Path' (Rel WaspProjectDir) File' -> Bool
+    doesConfigFileExist file =
+      isJust $ find ((==) file . CF._pathInWaspProjectDir) configFileRelocators
 
--- | Establishes the mapping of what config files to copy and where from/to.
+-- Establishes the mapping of what config files to copy and where from/to.
 -- NOTE: In the future, we could allow devs to configure what files we look for and where we copy them.
 configFileRelocationMap :: ConfigFileRelocationMap
 configFileRelocationMap =
diff --git a/waspc/src/Wasp/Generator/ExternalConfig/PackageJson.hs b/waspc/src/Wasp/Generator/ExternalConfig/PackageJson.hs
index f435502614..2f29812c51 100644
--- a/waspc/src/Wasp/Generator/ExternalConfig/PackageJson.hs
+++ b/waspc/src/Wasp/Generator/ExternalConfig/PackageJson.hs
@@ -7,22 +7,29 @@ import qualified Data.Map as M
 import qualified Wasp.ExternalConfig.PackageJson as P
 import Wasp.Generator.Common (prismaVersion)
 import Wasp.Generator.ExternalConfig.Common (ErrorMsg)
+import Wasp.Generator.SdkGenerator.Common (tailwindCssVersion)
 import Wasp.Generator.WebAppGenerator.Common (reactRouterVersion, reactVersion)
 
-validatePackageJson :: P.PackageJson -> [ErrorMsg]
-validatePackageJson packageJson =
+validatePackageJson :: Bool -> P.PackageJson -> [ErrorMsg]
+validatePackageJson isTailwindUsed packageJson =
   concat
-    [ validate ("wasp", "file:.wasp/out/sdk/wasp") IsListedWithExactVersion,
-      validate ("prisma", show prismaVersion) IsListedAsDevWithExactVersion,
-      -- Installing the wrong version of "react-router-dom" can make users believe that they
-      -- can use features that are not available in the version that Wasp supports.
-      validate ("react-router-dom", show reactRouterVersion) IsListedWithExactVersion,
-      validate ("react", show reactVersion) IsListedWithExactVersion,
-      validate ("react-dom", show reactVersion) IsListedWithExactVersion
-    ]
+    ( [ validate ("wasp", "file:.wasp/out/sdk/wasp") IsListedWithExactVersion,
+        validate ("prisma", show prismaVersion) IsListedAsDevWithExactVersion,
+        -- Installing the wrong version of "react-router-dom" can make users believe that they
+        -- can use features that are not available in the version that Wasp supports.
+        validate ("react-router-dom", show reactRouterVersion) IsListedWithExactVersion,
+        validate ("react", show reactVersion) IsListedWithExactVersion,
+        validate ("react-dom", show reactVersion) IsListedWithExactVersion
+      ]
+        ++ tailwindValidations
+    )
   where
     validate = validateDep packageJson
 
+    tailwindValidations =
+      [ validate ("tailwindcss", show tailwindCssVersion) IsListedWithExactVersion | isTailwindUsed
+      ]
+
 data PackageValidationType = IsListedWithExactVersion | IsListedAsDevWithExactVersion | HasExactVersionIfListed
 
 validateDep :: P.PackageJson -> (P.PackageName, P.PackageVersion) -> PackageValidationType -> [String]
diff --git a/waspc/src/Wasp/Generator/SdkGenerator.hs b/waspc/src/Wasp/Generator/SdkGenerator.hs
index 26906464c6..e595e54dd4 100644
--- a/waspc/src/Wasp/Generator/SdkGenerator.hs
+++ b/waspc/src/Wasp/Generator/SdkGenerator.hs
@@ -44,6 +44,7 @@ import Wasp.Generator.SdkGenerator.Client.AuthG (genNewClientAuth)
 import Wasp.Generator.SdkGenerator.Client.CrudG (genNewClientCrudApi)
 import qualified Wasp.Generator.SdkGenerator.Client.OperationsGenerator as ClientOpsGen
 import Wasp.Generator.SdkGenerator.Client.RouterGenerator (genNewClientRouterApi)
+import Wasp.Generator.SdkGenerator.Common (tailwindCssVersion)
 import qualified Wasp.Generator.SdkGenerator.Common as C
 import Wasp.Generator.SdkGenerator.CrudG (genCrud)
 import Wasp.Generator.SdkGenerator.EnvValidation (depsRequiredByEnvValidation, genEnvValidation)
@@ -279,10 +280,10 @@ depsRequiredForAuth spec = maybe [] (const authDeps) maybeAuth
 
 depsRequiredByTailwind :: AppSpec -> [AS.Dependency.Dependency]
 depsRequiredByTailwind spec =
-  if G.CF.isTailwindUsed spec
+  if G.CF.isTailwindUsed $ AS.configFiles spec
     then
       AS.Dependency.fromList
-        [ ("tailwindcss", "^3.2.7"),
+        [ ("tailwindcss", show tailwindCssVersion),
           ("postcss", "^8.4.21"),
           ("autoprefixer", "^10.4.13")
         ]
diff --git a/waspc/src/Wasp/Generator/SdkGenerator/Common.hs b/waspc/src/Wasp/Generator/SdkGenerator/Common.hs
index 5a0311e13f..87fd5f5e85 100644
--- a/waspc/src/Wasp/Generator/SdkGenerator/Common.hs
+++ b/waspc/src/Wasp/Generator/SdkGenerator/Common.hs
@@ -10,6 +10,7 @@ import Wasp.Generator.ExternalCodeGenerator.Common (GeneratedExternalCodeDir)
 import Wasp.Generator.FileDraft (FileDraft, createTemplateFileDraft)
 import Wasp.Generator.Templates (TemplatesDir)
 import Wasp.Project.Common (generatedCodeDirInDotWaspDir)
+import qualified Wasp.SemanticVersion as SV
 import Wasp.Util (toUpperFirst)
 
 data SdkRootDir
@@ -84,3 +85,6 @@ serverTemplatesDirInSdkTemplatesDir = [reldir|server|]
 
 getOperationTypeName :: AS.Operation.Operation -> String
 getOperationTypeName operation = toUpperFirst (AS.Operation.getName operation) ++ "_ext"
+
+tailwindCssVersion :: SV.ComparatorSet
+tailwindCssVersion = SV.backwardsCompatibleWith $ SV.Version 3 2 7
diff --git a/waspc/src/Wasp/Project/Analyze.hs b/waspc/src/Wasp/Project/Analyze.hs
index 235c29df26..cf12939d5c 100644
--- a/waspc/src/Wasp/Project/Analyze.hs
+++ b/waspc/src/Wasp/Project/Analyze.hs
@@ -14,6 +14,7 @@ import StrongPath
     fromAbsDir,
   )
 import qualified Wasp.AppSpec as AS
+import qualified Wasp.AppSpec.ConfigFile as CF
 import Wasp.AppSpec.Core.Decl.JSON ()
 import qualified Wasp.AppSpec.Valid as ASV
 import Wasp.CompileOptions (CompileOptions)
@@ -51,6 +52,10 @@ analyzeWaspProject ::
   IO (Either [CompileError] AS.AppSpec, [CompileWarning])
 analyzeWaspProject waspDir options = do
   waspFilePathOrError <- left (: []) <$> findWaspFile waspDir
+  configFiles <- CF.discoverConfigFiles waspDir G.CF.configFileRelocationMap
+
+  let isTailwindUsed = G.CF.isTailwindUsed configFiles
+
   case waspFilePathOrError of
     Left err -> return (Left err, [])
     Right waspFilePath ->
@@ -61,25 +66,25 @@ analyzeWaspProject waspDir options = do
           analyzeWaspFile waspDir prismaSchemaAst waspFilePath >>= \case
             Left errors -> return (Left errors, [])
             Right declarations ->
-              EC.analyzeExternalConfigs waspDir (getSrcTsConfigInWaspProjectDir waspFilePath) >>= \case
+              EC.analyzeExternalConfigs isTailwindUsed waspDir (getSrcTsConfigInWaspProjectDir waspFilePath) >>= \case
                 Left errors -> return (Left errors, [])
-                Right externalConfigs -> constructAppSpec waspDir options externalConfigs prismaSchemaAst declarations
+                Right externalConfigs -> constructAppSpec waspDir options externalConfigs configFiles prismaSchemaAst declarations
 
 constructAppSpec ::
   Path' Abs (Dir WaspProjectDir) ->
   CompileOptions ->
   EC.ExternalConfigs ->
+  [CF.ConfigFileRelocator] ->
   Psl.Schema.Schema ->
   [AS.Decl] ->
   IO (Either [CompileError] AS.AppSpec, [CompileWarning])
-constructAppSpec waspDir options externalConfigs parsedPrismaSchema decls = do
+constructAppSpec waspDir options externalConfigs configFiles parsedPrismaSchema decls = do
   externalCodeFiles <- ExternalFiles.readCodeFiles waspDir
   externalPublicFiles <- ExternalFiles.readPublicFiles waspDir
   customViteConfigPath <- findCustomViteConfigPath waspDir
 
   maybeMigrationsDir <- findMigrationsDir waspDir
   maybeUserDockerfileContents <- loadUserDockerfileContents waspDir
-  configFiles <- CF.discoverConfigFiles waspDir G.CF.configFileRelocationMap
   let dbSystem = getValidDbSystemFromPrismaSchema parsedPrismaSchema
   let devDbUrl = makeDevDatabaseUrl waspDir dbSystem decls
   serverEnvVars <- readDotEnvServer waspDir
diff --git a/waspc/src/Wasp/Project/ExternalConfig.hs b/waspc/src/Wasp/Project/ExternalConfig.hs
index 742d67285d..8a1effb462 100644
--- a/waspc/src/Wasp/Project/ExternalConfig.hs
+++ b/waspc/src/Wasp/Project/ExternalConfig.hs
@@ -23,11 +23,12 @@ data ExternalConfigs = ExternalConfigs
   deriving (Show)
 
 analyzeExternalConfigs ::
+  Bool ->
   Path' Abs (Dir WaspProjectDir) ->
   Path' (Rel WaspProjectDir) (File SrcTsConfigFile) ->
   IO (Either [CompileError] ExternalConfigs)
-analyzeExternalConfigs waspDir srcTsConfigFile = runExceptT $ do
-  packageJsonContent <- ExceptT $ analyzePackageJsonFile waspDir
+analyzeExternalConfigs isTailwindUsed waspDir srcTsConfigFile = runExceptT $ do
+  packageJsonContent <- ExceptT $ analyzePackageJsonFile isTailwindUsed waspDir
   tsConfigContent <- ExceptT $ analyzeSrcTsConfigFile waspDir srcTsConfigFile
 
   return $
diff --git a/waspc/src/Wasp/Project/ExternalConfig/PackageJson.hs b/waspc/src/Wasp/Project/ExternalConfig/PackageJson.hs
index 562285a8b6..e1f5d50d84 100644
--- a/waspc/src/Wasp/Project/ExternalConfig/PackageJson.hs
+++ b/waspc/src/Wasp/Project/ExternalConfig/PackageJson.hs
@@ -18,11 +18,11 @@ import Wasp.Project.Common
   )
 import qualified Wasp.Util.IO as IOUtil
 
-analyzePackageJsonFile :: Path' Abs (Dir WaspProjectDir) -> IO (Either [String] P.PackageJson)
-analyzePackageJsonFile waspProjectDir = runExceptT $ do
+analyzePackageJsonFile :: Bool -> Path' Abs (Dir WaspProjectDir) -> IO (Either [String] P.PackageJson)
+analyzePackageJsonFile isTailwindUsed waspProjectDir = runExceptT $ do
   packageJsonFile <- ExceptT findPackageJsonFileOrError
   packageJson <- ExceptT $ readPackageJsonFile packageJsonFile
-  case validatePackageJson packageJson of
+  case validatePackageJson isTailwindUsed packageJson of
     [] -> return packageJson
     errors -> throwError errors
   where
diff --git a/waspc/waspc.cabal b/waspc/waspc.cabal
index d8af354554..a70ea00b5a 100644
--- a/waspc/waspc.cabal
+++ b/waspc/waspc.cabal
@@ -304,7 +304,6 @@ library
     Wasp.Generator.NpmInstall
     Wasp.Generator.NpmInstall.Common
     Wasp.Generator.NpmInstall.InstalledNpmDepsLog
-    Wasp.Generator.ImportPathAlias
     Wasp.Generator.SdkGenerator
     Wasp.Generator.SdkGenerator.Auth.AuthFormsG
     Wasp.Generator.SdkGenerator.Auth.EmailAuthG