diff --git a/packages/@tailwindcss-upgrade/src/index.ts b/packages/@tailwindcss-upgrade/src/index.ts
index 3f57ef1987b1..15d11b733d93 100644
--- a/packages/@tailwindcss-upgrade/src/index.ts
+++ b/packages/@tailwindcss-upgrade/src/index.ts
@@ -84,7 +84,7 @@ async function run() {
     // Load and parse all stylesheets
     for (let result of loadResults) {
       if (result.status === 'rejected') {
-        error(`${result.reason}`)
+        error(`${result.reason?.message ?? result.reason}`, { prefix: '↳ ' })
       }
     }
 
@@ -95,8 +95,8 @@ async function run() {
     // Analyze the stylesheets
     try {
       await analyzeStylesheets(stylesheets)
-    } catch (e: unknown) {
-      error(`${e}`)
+    } catch (e: any) {
+      error(`${e?.message ?? e}`, { prefix: '↳ ' })
     }
 
     // Ensure stylesheets are linked to configs
@@ -105,12 +105,14 @@ async function run() {
         configPath: flags['--config'],
         base,
       })
-    } catch (e: unknown) {
-      error(`${e}`)
+    } catch (e: any) {
+      error(`${e?.message ?? e}`, { prefix: '↳ ' })
     }
 
     // Migrate js config files, linked to stylesheets
-    info('Migrating JavaScript configuration files…')
+    if (stylesheets.some((sheet) => sheet.isTailwindRoot)) {
+      info('Migrating JavaScript configuration files…')
+    }
     let configBySheet = new Map<Stylesheet, Awaited<ReturnType<typeof prepareConfig>>>()
     let jsConfigMigrationBySheet = new Map<
       Stylesheet,
@@ -136,13 +138,16 @@ async function run() {
 
       if (jsConfigMigration !== null) {
         success(
-          `↳ Migrated configuration file: ${highlight(relative(config.configFilePath, base))}`,
+          `Migrated configuration file: ${highlight(relative(config.configFilePath, base))}`,
+          { prefix: '↳ ' },
         )
       }
     }
 
     // Migrate source files, linked to config files
-    info('Migrating templates…')
+    if (configBySheet.size > 0) {
+      info('Migrating templates…')
+    }
     {
       // Template migrations
       for (let config of configBySheet.values()) {
@@ -168,43 +173,44 @@ async function run() {
         )
 
         success(
-          `↳ Migrated templates for configuration file: ${highlight(relative(config.configFilePath, base))}`,
+          `Migrated templates for configuration file: ${highlight(relative(config.configFilePath, base))}`,
+          { prefix: '↳ ' },
         )
       }
     }
 
     // Migrate each CSS file
-    info('Migrating stylesheets…')
-    let migrateResults = await Promise.allSettled(
-      stylesheets.map((sheet) => {
-        let config = configBySheet.get(sheet)!
-        let jsConfigMigration = jsConfigMigrationBySheet.get(sheet)!
-
-        if (!config) {
-          for (let parent of sheet.ancestors()) {
-            if (parent.isTailwindRoot) {
-              config ??= configBySheet.get(parent)!
-              jsConfigMigration ??= jsConfigMigrationBySheet.get(parent)!
-              break
+    if (stylesheets.length > 0) {
+      info('Migrating stylesheets…')
+    }
+    await Promise.all(
+      stylesheets.map(async (sheet) => {
+        try {
+          let config = configBySheet.get(sheet)!
+          let jsConfigMigration = jsConfigMigrationBySheet.get(sheet)!
+
+          if (!config) {
+            for (let parent of sheet.ancestors()) {
+              if (parent.isTailwindRoot) {
+                config ??= configBySheet.get(parent)!
+                jsConfigMigration ??= jsConfigMigrationBySheet.get(parent)!
+                break
+              }
             }
           }
-        }
 
-        return migrateStylesheet(sheet, { ...config, jsConfigMigration })
+          await migrateStylesheet(sheet, { ...config, jsConfigMigration })
+        } catch (e: any) {
+          error(`${e?.message ?? e} in ${highlight(relative(sheet.file!, base))}`, { prefix: '↳ ' })
+        }
       }),
     )
 
-    for (let result of migrateResults) {
-      if (result.status === 'rejected') {
-        error(`${result.reason}`)
-      }
-    }
-
     // Split up stylesheets (as needed)
     try {
       await splitStylesheets(stylesheets)
-    } catch (e: unknown) {
-      error(`${e}`)
+    } catch (e: any) {
+      error(`${e?.message ?? e}`, { prefix: '↳ ' })
     }
 
     // Cleanup `@import "…" layer(utilities)`
@@ -241,7 +247,7 @@ async function run() {
       await fs.writeFile(sheet.file, sheet.root.toString())
 
       if (sheet.isTailwindRoot) {
-        success(`↳ Migrated stylesheet: ${highlight(relative(sheet.file, base))}`)
+        success(`Migrated stylesheet: ${highlight(relative(sheet.file, base))}`, { prefix: '↳ ' })
       }
     }
   }
@@ -260,7 +266,7 @@ async function run() {
   try {
     // Upgrade Tailwind CSS
     await pkg(base).add(['tailwindcss@next'])
-    success(`↳ Updated package: ${highlight('tailwindcss')}`)
+    success(`Updated package: ${highlight('tailwindcss')}`, { prefix: '↳ ' })
   } catch {}
 
   // Run all cleanup functions because we completed the migration
diff --git a/packages/@tailwindcss-upgrade/src/migrate-js-config.ts b/packages/@tailwindcss-upgrade/src/migrate-js-config.ts
index b69379df1f7d..e17bf9601c75 100644
--- a/packages/@tailwindcss-upgrade/src/migrate-js-config.ts
+++ b/packages/@tailwindcss-upgrade/src/migrate-js-config.ts
@@ -44,7 +44,8 @@ export async function migrateJsConfig(
 
   if (!canMigrateConfig(unresolvedConfig, source)) {
     info(
-      `↳ The configuration file at ${highlight(relative(fullConfigPath, base))} could not be automatically migrated to the new CSS configuration format, so your CSS has been updated to load your existing configuration file.`,
+      `The configuration file at ${highlight(relative(fullConfigPath, base))} could not be automatically migrated to the new CSS configuration format, so your CSS has been updated to load your existing configuration file.`,
+      { prefix: '↳ ' },
     )
     return null
   }
diff --git a/packages/@tailwindcss-upgrade/src/migrate-postcss.ts b/packages/@tailwindcss-upgrade/src/migrate-postcss.ts
index 1bfb2caa80f1..286884522bdd 100644
--- a/packages/@tailwindcss-upgrade/src/migrate-postcss.ts
+++ b/packages/@tailwindcss-upgrade/src/migrate-postcss.ts
@@ -92,7 +92,7 @@ export async function migratePostCSSConfig(base: string) {
     if (location !== null) {
       try {
         await pkg(base).add(['@tailwindcss/postcss@next'], location)
-        success(`↳ Installed package: ${highlight('@tailwindcss/postcss')}`)
+        success(`Installed package: ${highlight('@tailwindcss/postcss')}`, { prefix: '↳ ' })
       } catch {}
     }
   }
@@ -104,13 +104,15 @@ export async function migratePostCSSConfig(base: string) {
       ].filter(Boolean) as string[]
       await pkg(base).remove(packagesToRemove)
       for (let pkg of packagesToRemove) {
-        success(`↳ Removed package: ${highlight(pkg)}`)
+        success(`Removed package: ${highlight(pkg)}`, { prefix: '↳ ' })
       }
     } catch {}
   }
 
   if (didMigrate && jsConfigPath) {
-    success(`↳ Migrated PostCSS configuration: ${highlight(relative(jsConfigPath, base))}`)
+    success(`Migrated PostCSS configuration: ${highlight(relative(jsConfigPath, base))}`, {
+      prefix: '↳ ',
+    })
   }
 }
 
diff --git a/packages/@tailwindcss-upgrade/src/migrate-prettier.ts b/packages/@tailwindcss-upgrade/src/migrate-prettier.ts
index 7edf34f47a36..cd56cc6880e1 100644
--- a/packages/@tailwindcss-upgrade/src/migrate-prettier.ts
+++ b/packages/@tailwindcss-upgrade/src/migrate-prettier.ts
@@ -9,7 +9,7 @@ export async function migratePrettierPlugin(base: string) {
     let packageJson = await fs.readFile(packageJsonPath, 'utf-8')
     if (packageJson.includes('prettier-plugin-tailwindcss')) {
       await pkg(base).add(['prettier-plugin-tailwindcss@latest'])
-      success(`↳ Updated package: ${highlight('prettier-plugin-tailwindcss')}`)
+      success(`Updated package: ${highlight('prettier-plugin-tailwindcss')}`, { prefix: '↳ ' })
     }
   } catch {}
 }
diff --git a/packages/@tailwindcss-upgrade/src/migrate.ts b/packages/@tailwindcss-upgrade/src/migrate.ts
index a3f2e344adda..932a0a726b22 100644
--- a/packages/@tailwindcss-upgrade/src/migrate.ts
+++ b/packages/@tailwindcss-upgrade/src/migrate.ts
@@ -120,8 +120,10 @@ export async function analyze(stylesheets: Stylesheet[]) {
               resolvedPath = resolveCssId(id, basePath)
             }
           } catch (err) {
-            console.warn(`Failed to resolve import: ${id}. Skipping.`)
-            console.error(err)
+            error(
+              `Failed to resolve import: ${highlight(id)} in ${highlight(relative(node.source?.input.file!, basePath))}. Skipping.`,
+              { prefix: '↳ ' },
+            )
             return
           }
 
@@ -334,10 +336,12 @@ export async function analyze(stylesheets: Stylesheet[]) {
     }
   }
 
-  let error = `You have one or more stylesheets that are imported into a utility layer and non-utility layer.\n`
-  error += `We cannot convert stylesheets under these conditions. Please look at the following stylesheets:\n`
+  {
+    let error = `You have one or more stylesheets that are imported into a utility layer and non-utility layer.\n`
+    error += `We cannot convert stylesheets under these conditions. Please look at the following stylesheets:\n`
 
-  throw new Error(error + lines.join('\n'))
+    throw new Error(error + lines.join('\n'))
+  }
 }
 
 export async function linkConfigs(
@@ -347,7 +351,7 @@ export async function linkConfigs(
   let rootStylesheets = stylesheets.filter((sheet) => sheet.isTailwindRoot)
   if (rootStylesheets.length === 0) {
     throw new Error(
-      'Cannot find any CSS files that reference Tailwind CSS.\nBefore your project can be upgraded you need to create a CSS file that imports Tailwind CSS or uses `@tailwind`.',
+      `Cannot find any CSS files that reference Tailwind CSS.\nBefore your project can be upgraded you need to create a CSS file that imports Tailwind CSS or uses ${highlight('@tailwind')}.`,
     )
   }
   let withoutAtConfig = rootStylesheets.filter((sheet) => {
@@ -396,6 +400,7 @@ export async function linkConfigs(
     for (let sheet of problematicStylesheets) {
       error(
         `Could not determine configuration file for: ${highlight(relative(sheet.file!, base))}\nUpdate your stylesheet to use ${highlight('@config')} to specify the correct configuration file explicitly and then run the upgrade tool again.`,
+        { prefix: '↳ ' },
       )
     }
 
@@ -407,7 +412,8 @@ export async function linkConfigs(
     try {
       if (!sheet || !sheet.file) return
       success(
-        `↳ Linked ${highlight(relativePath(configPath, base))} to ${highlight(relativePath(sheet.file, base))}`,
+        `Linked ${highlight(relativePath(configPath, base))} to ${highlight(relativePath(sheet.file, base))}`,
+        { prefix: '↳ ' },
       )
 
       // Link the `@config` directive to the root stylesheets
@@ -447,7 +453,7 @@ export async function linkConfigs(
         }
       }
     } catch (e: any) {
-      error('Could not load the configuration file: ' + e.message)
+      error('Could not load the configuration file: ' + e.message, { prefix: '↳ ' })
       process.exit(1)
     }
   }
diff --git a/packages/@tailwindcss-upgrade/src/template/prepare-config.ts b/packages/@tailwindcss-upgrade/src/template/prepare-config.ts
index a151b6ab46c5..f5a817d40ea3 100644
--- a/packages/@tailwindcss-upgrade/src/template/prepare-config.ts
+++ b/packages/@tailwindcss-upgrade/src/template/prepare-config.ts
@@ -65,7 +65,7 @@ export async function prepareConfig(
       configFilePath,
     }
   } catch (e: any) {
-    error('Could not load the configuration file: ' + e.message)
+    error('Could not load the configuration file: ' + e.message, { prefix: '↳ ' })
     process.exit(1)
   }
 }
diff --git a/packages/@tailwindcss-upgrade/src/utils/extract-static-plugins.ts b/packages/@tailwindcss-upgrade/src/utils/extract-static-plugins.ts
index d0f6dbf8e2f4..4318c14ef36e 100644
--- a/packages/@tailwindcss-upgrade/src/utils/extract-static-plugins.ts
+++ b/packages/@tailwindcss-upgrade/src/utils/extract-static-plugins.ts
@@ -272,8 +272,8 @@ export function findStaticPlugins(source: string): [string, null | StaticPluginO
       }
     }
     return plugins
-  } catch (error) {
-    console.error(error)
+  } catch (error: any) {
+    error(`${error?.message ?? error}`, { prefix: '↳ ' })
     return null
   }
 }
diff --git a/packages/@tailwindcss-upgrade/src/utils/renderer.ts b/packages/@tailwindcss-upgrade/src/utils/renderer.ts
index b902fe88d15d..38bd9826a0ab 100644
--- a/packages/@tailwindcss-upgrade/src/utils/renderer.ts
+++ b/packages/@tailwindcss-upgrade/src/utils/renderer.ts
@@ -89,32 +89,36 @@ export function indent(value: string, offset = 0) {
   return `${' '.repeat(offset + UI.indent)}${value}`
 }
 
-export function success(message: string, print = eprintln) {
-  wordWrap(message, process.stderr.columns - 3).map((line) => {
-    return print(`${pc.green('\u2502')} ${line}`)
+function log(message: string, { art = pc.gray('\u2502'), prefix = '', print = eprintln }) {
+  let prefixLength = prefix.length
+  let padding = ' '
+  let paddingLength = padding.length
+  let artLength = stripVTControlCharacters(art).length
+  let availableWidth = process.stderr.columns
+  let totalWidth = availableWidth - prefixLength - paddingLength * 2 - artLength
+
+  wordWrap(message, totalWidth).map((line, idx) => {
+    return print(
+      `${art}${padding}${idx === 0 ? prefix : ' '.repeat(prefixLength)}${line}${padding}`,
+    )
   })
   print()
 }
 
-export function info(message: string, print = eprintln) {
-  wordWrap(message, process.stderr.columns - 3).map((line) => {
-    return print(`${pc.blue('\u2502')} ${line}`)
-  })
-  print()
+export function success(message: string, { prefix = '', print = eprintln } = {}) {
+  log(message, { art: pc.green('\u2502'), prefix, print })
 }
 
-export function error(message: string, print = eprintln) {
-  wordWrap(message, process.stderr.columns - 3).map((line) => {
-    return print(`${pc.red('\u2502')} ${line}`)
-  })
-  print()
+export function info(message: string, { prefix = '', print = eprintln } = {}) {
+  log(message, { art: pc.blue('\u2502'), prefix, print })
 }
 
-export function warn(message: string, print = eprintln) {
-  wordWrap(message, process.stderr.columns - 3).map((line) => {
-    return print(`${pc.yellow('\u2502')} ${line}`)
-  })
-  print()
+export function error(message: string, { prefix = '', print = eprintln } = {}) {
+  log(message, { art: pc.red('\u2502'), prefix, print })
+}
+
+export function warn(message: string, { prefix = '', print = eprintln } = {}) {
+  log(message, { art: pc.yellow('\u2502'), prefix, print })
 }
 
 // Rust inspired functions to print to the console:
diff --git a/packages/tailwindcss/src/at-import.ts b/packages/tailwindcss/src/at-import.ts
index e5b937c71c3b..8066abd98ff9 100644
--- a/packages/tailwindcss/src/at-import.ts
+++ b/packages/tailwindcss/src/at-import.ts
@@ -85,7 +85,7 @@ export function parseImportParams(params: ValueParser.ValueAstNode[]) {
     }
 
     if (node.kind === 'function' && node.value.toLowerCase() === 'url') {
-      throw new Error('url functions are not supported')
+      throw new Error('`url(…)` functions are not supported')
     }
 
     if (!uri) throw new Error('Unable to find uri')
@@ -95,7 +95,7 @@ export function parseImportParams(params: ValueParser.ValueAstNode[]) {
       node.value.toLowerCase() === 'layer'
     ) {
       if (layer) throw new Error('Multiple layers')
-      if (supports) throw new Error('layers must be defined before support conditions')
+      if (supports) throw new Error('`layer(…)` must be defined before `supports(…)` conditions')
 
       if ('nodes' in node) {
         layer = ValueParser.toCss(node.nodes)