diff --git a/Cargo.lock b/Cargo.lock
index 2126fe9241..618dceb1d6 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2342,6 +2342,7 @@ dependencies = [
  "derive-new",
  "getset",
  "indexmap",
+ "itertools",
  "log",
  "natural",
  "nu-build",
diff --git a/crates/nu-cli/src/commands/autoview.rs b/crates/nu-cli/src/commands/autoview.rs
index ab4e56425d..fe082187f6 100644
--- a/crates/nu-cli/src/commands/autoview.rs
+++ b/crates/nu-cli/src/commands/autoview.rs
@@ -84,6 +84,10 @@ pub fn autoview(context: RunnableContext) -> Result<OutputStream, ShellError> {
         Some(val) => val.is_true(),
         _ => false,
     };
+    let pivot_to_fit = match config::config(Tag::unknown())?.get("pivot_to_fit") {
+        Some(val) => val.is_true(),
+        _ => false,
+    };
 
     Ok(OutputStream::new(async_stream! {
         let (mut input_stream, context) = RunnableContextWithoutInput::convert(context);
@@ -221,7 +225,14 @@ pub fn autoview(context: RunnableContext) -> Result<OutputStream, ShellError> {
                                 yield Err(e);
                             }
 
-                            Value { value: UntaggedValue::Row(row), ..} if !no_auto_pivot => {
+                            Value { value: UntaggedValue::Row(row), ..} if !no_auto_pivot
+                                || (pivot_to_fit && // Or if the row character count + number of headers * 2 (for padding) > terminal width
+                                (row.entries.iter().map(|(k,v)| v.convert_to_string())
+                                .collect::<Vec<_>>().iter()
+                                .fold(0, |acc, len| acc + len.len())
+                                +
+                                (row.entries.iter().map(|(k,_)| k.chars()).count() * 2))
+                                > textwrap::termwidth()) => {
                                 use prettytable::format::{FormatBuilder, LinePosition, LineSeparator};
                                 use prettytable::{color, Attr, Cell, Row, Table};
                                 use crate::data::value::{format_leaf, style_leaf};
diff --git a/crates/nu-protocol/Cargo.toml b/crates/nu-protocol/Cargo.toml
index d490a081e5..0b413769d3 100644
--- a/crates/nu-protocol/Cargo.toml
+++ b/crates/nu-protocol/Cargo.toml
@@ -29,6 +29,7 @@ query_interface = "0.3.5"
 byte-unit = "3.0.3"
 natural = "0.5.0"
 log = "0.4.8"
+itertools = "0.9.0"
 
 # implement conversions
 serde_yaml = "0.8"
diff --git a/crates/nu-protocol/src/value.rs b/crates/nu-protocol/src/value.rs
index b55c126dbf..c0403982df 100644
--- a/crates/nu-protocol/src/value.rs
+++ b/crates/nu-protocol/src/value.rs
@@ -15,10 +15,11 @@ use crate::value::dict::Dictionary;
 use crate::value::iter::{RowValueIter, TableValueIter};
 use crate::value::primitive::Primitive;
 use crate::value::range::{Range, RangeInclusion};
-use crate::{ColumnPath, PathMember};
+use crate::{ColumnPath, PathMember, UnspannedPathMember};
 use bigdecimal::BigDecimal;
 use chrono::{DateTime, Utc};
 use indexmap::IndexMap;
+use itertools::Itertools;
 use nu_errors::ShellError;
 use nu_source::{AnchorLocation, HasSpan, Span, Spanned, Tag};
 use num_bigint::BigInt;
@@ -274,6 +275,35 @@ impl Value {
         }
     }
 
+    pub fn convert_to_string(&self) -> String {
+        match &self.value {
+            UntaggedValue::Primitive(Primitive::String(s)) => s.clone(),
+            UntaggedValue::Primitive(Primitive::Date(dt)) => dt.format("%Y-%b-%d").to_string(),
+            UntaggedValue::Primitive(Primitive::Boolean(x)) => format!("{}", x),
+            UntaggedValue::Primitive(Primitive::Decimal(x)) => format!("{}", x),
+            UntaggedValue::Primitive(Primitive::Int(x)) => format!("{}", x),
+            UntaggedValue::Primitive(Primitive::Bytes(x)) => format!("{}", x),
+            UntaggedValue::Primitive(Primitive::Path(x)) => format!("{}", x.display()),
+            UntaggedValue::Primitive(Primitive::ColumnPath(path)) => {
+                let joined = path
+                    .iter()
+                    .map(|member| match &member.unspanned {
+                        UnspannedPathMember::String(name) => name.to_string(),
+                        UnspannedPathMember::Int(n) => format!("{}", n),
+                    })
+                    .join(".");
+
+                if joined.contains(' ') {
+                    format!("\"{}\"", joined)
+                } else {
+                    joined
+                }
+            }
+
+            _ => String::from(""),
+        }
+    }
+
     pub fn format(&self, fmt: &str) -> Result<String, ShellError> {
         match &self.value {
             UntaggedValue::Primitive(Primitive::Date(dt)) => Ok(dt.format(fmt).to_string()),