diff --git a/compiler/src/dotty/tools/dotc/config/CliCommand.scala b/compiler/src/dotty/tools/dotc/config/CliCommand.scala
index 1a48fbfdf131..e361519bb54d 100644
--- a/compiler/src/dotty/tools/dotc/config/CliCommand.scala
+++ b/compiler/src/dotty/tools/dotc/config/CliCommand.scala
@@ -66,9 +66,39 @@ trait CliCommand:
 
   /** Creates a help message for a subset of options based on cond */
   protected def availableOptionsMsg(cond: Setting[?] => Boolean)(using settings: ConcreteSettings)(using SettingsState): String =
-    val ss                  = (settings.allSettings filter cond).toList sortBy (_.name)
-    val width               = (ss map (_.name.length)).max
-    def format(s: String)   = ("%-" + width + "s") format s
+    val ss = (settings.allSettings filter cond).toList sortBy (_.name)
+    val maxNameWidth = 30
+    val nameWidths = ss.map(_.name.length).partition(_ < maxNameWidth)._1
+    val width = if nameWidths.nonEmpty then nameWidths.max else maxNameWidth
+    val terminalWidth = settings.pageWidth.value
+    val (nameWidth, descriptionWidth) = {
+      val w1 =
+        if width < maxNameWidth then width
+        else maxNameWidth
+      val w2 =
+        if terminalWidth < w1 + maxNameWidth then 0
+        else terminalWidth - w1 - 1
+      (w1, w2)
+    }
+    def formatName(name: String) =
+      if name.length <= nameWidth then ("%-" + nameWidth + "s") format name
+      else (name + "\n%-" + nameWidth + "s") format ""
+    def formatDescription(text: String): String =
+      if descriptionWidth == 0 then text
+      else if text.length < descriptionWidth then text
+      else {
+        val inx = text.substring(0, descriptionWidth).lastIndexOf(" ")
+        if inx < 0 then text
+        else
+          val str = text.substring(0, inx)
+          s"${str}\n${formatName("")} ${formatDescription(text.substring(inx + 1))}"
+      }
+    def formatSetting(name: String, value: String) =
+      if (value.nonEmpty)
+        // the format here is helping to make empty padding and put the additional information exactly under the description.
+        s"\n${formatName("")} $name: $value."
+      else
+        ""
     def helpStr(s: Setting[?]) =
       def defaultValue = s.default match
         case _: Int | _: String => s.default.toString
@@ -76,16 +106,8 @@ trait CliCommand:
           // For now, skip the default values that do not make sense for the end user.
           // For example 'false' for the version command.
           ""
-
-      def formatSetting(name: String, value: String) =
-        if (value.nonEmpty)
-        // the format here is helping to make empty padding and put the additional information exactly under the description.
-          s"\n${format("")} $name: $value."
-        else
-          ""
-      s"${format(s.name)} ${s.description}${formatSetting("Default", defaultValue)}${formatSetting("Choices", s.legalChoices)}"
-
-    ss.map(helpStr).mkString("", "\n", s"\n${format("@<file>")} A text file containing compiler arguments (options and source files).\n")
+      s"${formatName(s.name)} ${formatDescription(s.description)}${formatSetting("Default", defaultValue)}${formatSetting("Choices", s.legalChoices)}"
+    ss.map(helpStr).mkString("", "\n", s"\n${formatName("@<file>")} ${formatDescription("A text file containing compiler arguments (options and source files).")}\n")
 
   protected def shortUsage: String = s"Usage: $cmdName <options> <source files>"
 
diff --git a/compiler/src/dotty/tools/dotc/config/ScalaSettings.scala b/compiler/src/dotty/tools/dotc/config/ScalaSettings.scala
index 7506976fa212..19e5a4cea229 100644
--- a/compiler/src/dotty/tools/dotc/config/ScalaSettings.scala
+++ b/compiler/src/dotty/tools/dotc/config/ScalaSettings.scala
@@ -11,6 +11,18 @@ import Settings.Setting
 trait CommonScalaSettings { self: Settings.SettingGroup =>
   protected def defaultClasspath: String = sys.env.getOrElse("CLASSPATH", ".")
 
+  protected def defaultPageWidth: Int = {
+    val defaultWidth = 80
+    val columnsVar = System.getenv("COLUMNS")
+    if columnsVar != null then columnsVar.toInt
+    else if Properties.isWin then
+      val ansiconVar = System.getenv("ANSICON") // eg. "142x32766 (142x26)"
+      if ansiconVar != null && ansiconVar.matches("[0-9]+x.*") then
+        ansiconVar.substring(0, ansiconVar.indexOf("x")).toInt
+      else defaultWidth
+    else defaultWidth
+  }
+
   /** Path related settings */
   val bootclasspath: Setting[String] = PathSetting("-bootclasspath", "Override location of bootstrap class files.", Defaults.scalaBootClassPath, aliases = List("--boot-class-path"))
   val extdirs: Setting[String] = PathSetting("-extdirs", "Override location of installed extensions.", Defaults.scalaExtDirs, aliases = List("--extension-directories"))
@@ -26,7 +38,7 @@ trait CommonScalaSettings { self: Settings.SettingGroup =>
   val verbose: Setting[Boolean] = BooleanSetting("-verbose", "Output messages about what the compiler is doing.", aliases = List("--verbose"))
   val version: Setting[Boolean] = BooleanSetting("-version", "Print product version and exit.", aliases = List("--version"))
   val help: Setting[Boolean] = BooleanSetting("-help", "Print a synopsis of standard options.", aliases = List("--help"))
-  val pageWidth: Setting[Int] = IntSetting("-pagewidth", "Set page width", 80, aliases = List("--page-width"))
+  val pageWidth: Setting[Int] = IntSetting("-pagewidth", "Set page width", defaultPageWidth, aliases = List("--page-width"))
   val silentWarnings: Setting[Boolean] = BooleanSetting("-nowarn", "Silence all warnings.", aliases = List("--no-warnings"))
 
   /** Other settings */
diff --git a/dist/bin/common b/dist/bin/common
index da5ae4aeff66..a3847b2b1dbd 100755
--- a/dist/bin/common
+++ b/dist/bin/common
@@ -27,6 +27,12 @@ function onExit() {
 trap onExit INT TERM EXIT
 
 unset cygwin mingw msys darwin conemu
+
+# COLUMNS is used together with command line option '-pageWidth'.
+if command -v tput >/dev/null 2>&1; then
+  export COLUMNS="$(tput -Tdumb cols)"
+fi
+
 case "`uname`" in
   CYGWIN*) cygwin=true
           ;;