diff --git a/crates/nu-cli/src/completions/completer.rs b/crates/nu-cli/src/completions/completer.rs
index 0b1ac3f87b..5a15543141 100644
--- a/crates/nu-cli/src/completions/completer.rs
+++ b/crates/nu-cli/src/completions/completer.rs
@@ -122,11 +122,13 @@ impl NuCompleter {
             for pipeline_element in pipeline.elements {
                 match pipeline_element {
                     PipelineElement::Expression(_, expr)
-                    | PipelineElement::Redirection(_, _, expr)
+                    | PipelineElement::Redirection(_, _, expr, _)
                     | PipelineElement::And(_, expr)
                     | PipelineElement::Or(_, expr)
                     | PipelineElement::SameTargetRedirection { cmd: (_, expr), .. }
-                    | PipelineElement::SeparateRedirection { out: (_, expr), .. } => {
+                    | PipelineElement::SeparateRedirection {
+                        out: (_, expr, _), ..
+                    } => {
                         let flattened: Vec<_> = flatten_expression(&working_set, &expr);
                         let mut spans: Vec<String> = vec![];
 
diff --git a/crates/nu-cli/src/syntax_highlight.rs b/crates/nu-cli/src/syntax_highlight.rs
index babe1635da..3b7d9bdcb2 100644
--- a/crates/nu-cli/src/syntax_highlight.rs
+++ b/crates/nu-cli/src/syntax_highlight.rs
@@ -252,11 +252,11 @@ fn find_matching_block_end_in_block(
         for e in &p.elements {
             match e {
                 PipelineElement::Expression(_, e)
-                | PipelineElement::Redirection(_, _, e)
+                | PipelineElement::Redirection(_, _, e, _)
                 | PipelineElement::And(_, e)
                 | PipelineElement::Or(_, e)
                 | PipelineElement::SameTargetRedirection { cmd: (_, e), .. }
-                | PipelineElement::SeparateRedirection { out: (_, e), .. } => {
+                | PipelineElement::SeparateRedirection { out: (_, e, _), .. } => {
                     if e.span.contains(global_cursor_offset) {
                         if let Some(pos) = find_matching_block_end_in_expr(
                             line,
diff --git a/crates/nu-command/src/filesystem/save.rs b/crates/nu-command/src/filesystem/save.rs
index bad5bee609..4e9a5bda8e 100644
--- a/crates/nu-command/src/filesystem/save.rs
+++ b/crates/nu-command/src/filesystem/save.rs
@@ -1,7 +1,7 @@
 use nu_engine::current_dir;
 use nu_engine::CallExt;
 use nu_path::expand_path_with;
-use nu_protocol::ast::Call;
+use nu_protocol::ast::{Call, Expr, Expression};
 use nu_protocol::engine::{Command, EngineState, Stack};
 use nu_protocol::{
     Category, Example, PipelineData, RawStream, ShellError, Signature, Span, Spanned, SyntaxShape,
@@ -67,6 +67,24 @@ impl Command for Save {
         let append = call.has_flag("append");
         let force = call.has_flag("force");
         let progress = call.has_flag("progress");
+        let out_append = if let Some(Expression {
+            expr: Expr::Bool(out_append),
+            ..
+        }) = call.get_parser_info("out-append")
+        {
+            *out_append
+        } else {
+            false
+        };
+        let err_append = if let Some(Expression {
+            expr: Expr::Bool(err_append),
+            ..
+        }) = call.get_parser_info("err-append")
+        {
+            *err_append
+        } else {
+            false
+        };
 
         let span = call.head;
         let cwd = current_dir(engine_state, stack)?;
@@ -87,7 +105,7 @@ impl Command for Save {
         match input {
             PipelineData::ExternalStream { stdout: None, .. } => {
                 // Open files to possibly truncate them
-                let _ = get_files(&path, stderr_path.as_ref(), append, force)?;
+                let _ = get_files(&path, stderr_path.as_ref(), append, false, false, force)?;
                 Ok(PipelineData::empty())
             }
             PipelineData::ExternalStream {
@@ -95,7 +113,14 @@ impl Command for Save {
                 stderr,
                 ..
             } => {
-                let (file, stderr_file) = get_files(&path, stderr_path.as_ref(), append, force)?;
+                let (file, stderr_file) = get_files(
+                    &path,
+                    stderr_path.as_ref(),
+                    append,
+                    out_append,
+                    err_append,
+                    force,
+                )?;
 
                 // delegate a thread to redirect stderr to result.
                 let handler = stderr.map(|stderr_stream| match stderr_file {
@@ -127,7 +152,14 @@ impl Command for Save {
             PipelineData::ListStream(ls, _)
                 if raw || prepare_path(&path, append, force)?.0.extension().is_none() =>
             {
-                let (mut file, _) = get_files(&path, stderr_path.as_ref(), append, force)?;
+                let (mut file, _) = get_files(
+                    &path,
+                    stderr_path.as_ref(),
+                    append,
+                    out_append,
+                    err_append,
+                    force,
+                )?;
                 for val in ls {
                     file.write_all(&value_to_bytes(val)?)
                         .map_err(|err| ShellError::IOError(err.to_string()))?;
@@ -143,7 +175,14 @@ impl Command for Save {
                     input_to_bytes(input, Path::new(&path.item), raw, engine_state, stack, span)?;
 
                 // Only open file after successful conversion
-                let (mut file, _) = get_files(&path, stderr_path.as_ref(), append, force)?;
+                let (mut file, _) = get_files(
+                    &path,
+                    stderr_path.as_ref(),
+                    append,
+                    out_append,
+                    err_append,
+                    force,
+                )?;
 
                 file.write_all(&bytes)
                     .map_err(|err| ShellError::IOError(err.to_string()))?;
@@ -319,17 +358,19 @@ fn get_files(
     path: &Spanned<PathBuf>,
     stderr_path: Option<&Spanned<PathBuf>>,
     append: bool,
+    out_append: bool,
+    err_append: bool,
     force: bool,
 ) -> Result<(File, Option<File>), ShellError> {
     // First check both paths
-    let (path, path_span) = prepare_path(path, append, force)?;
+    let (path, path_span) = prepare_path(path, append || out_append, force)?;
     let stderr_path_and_span = stderr_path
         .as_ref()
-        .map(|stderr_path| prepare_path(stderr_path, append, force))
+        .map(|stderr_path| prepare_path(stderr_path, append || err_append, force))
         .transpose()?;
 
     // Only if both files can be used open and possibly truncate them
-    let file = open_file(path, path_span, append)?;
+    let file = open_file(path, path_span, append || out_append)?;
 
     let stderr_file = stderr_path_and_span
         .map(|(stderr_path, stderr_path_span)| {
@@ -342,7 +383,7 @@ fn get_files(
                     vec![],
                 ))
             } else {
-                open_file(stderr_path, stderr_path_span, append)
+                open_file(stderr_path, stderr_path_span, append || err_append)
             }
         })
         .transpose()?;
diff --git a/crates/nu-command/src/formats/from/nuon.rs b/crates/nu-command/src/formats/from/nuon.rs
index 8570ab9004..90f0ecd41d 100644
--- a/crates/nu-command/src/formats/from/nuon.rs
+++ b/crates/nu-command/src/formats/from/nuon.rs
@@ -124,7 +124,7 @@ impl Command for FromNuon {
             } else {
                 match pipeline.elements.remove(0) {
                     PipelineElement::Expression(_, expression)
-                    | PipelineElement::Redirection(_, _, expression)
+                    | PipelineElement::Redirection(_, _, expression, _)
                     | PipelineElement::And(_, expression)
                     | PipelineElement::Or(_, expression)
                     | PipelineElement::SameTargetRedirection {
@@ -132,7 +132,7 @@ impl Command for FromNuon {
                         ..
                     }
                     | PipelineElement::SeparateRedirection {
-                        out: (_, expression),
+                        out: (_, expression, _),
                         ..
                     } => expression,
                 }
diff --git a/crates/nu-command/tests/commands/redirection.rs b/crates/nu-command/tests/commands/redirection.rs
index f223d62f56..cae01dbbd9 100644
--- a/crates/nu-command/tests/commands/redirection.rs
+++ b/crates/nu-command/tests/commands/redirection.rs
@@ -12,6 +12,14 @@ fn redirect_err() {
         );
 
         assert!(output.out.contains("asdfasdfasdf.txt"));
+
+        // check append mode
+        let output = nu!(
+                cwd: dirs.test(),
+                "cat asdfasdfasdf.txt err>> a.txt; cat a.txt"
+        );
+        let v: Vec<_> = output.out.match_indices("asdfasdfasdf.txt").collect();
+        assert_eq!(v.len(), 2);
     })
 }
 
@@ -25,6 +33,12 @@ fn redirect_err() {
         );
 
         assert!(output.out.contains("true"));
+
+        let output = nu!(
+            cwd: dirs.test(),
+            "vol missingdrive err>> a; (open a | str stats).bytes >= 32"
+        );
+        assert!(output.out.contains("true"));
     })
 }
 
@@ -39,6 +53,10 @@ fn redirect_outerr() {
         let output = nu!(cwd: dirs.test(), "cat a");
 
         assert!(output.out.contains("asdfasdfasdf.txt"));
+
+        let output = nu!(cwd: dirs.test(), "cat asdfasdfasdf.txt o+e>> a; cat a");
+        let v: Vec<_> = output.out.match_indices("asdfasdfasdf.txt").collect();
+        assert_eq!(v.len(), 2);
     })
 }
 
@@ -53,6 +71,13 @@ fn redirect_outerr() {
         let output = nu!(cwd: dirs.test(), "(open a | str stats).bytes >= 16");
 
         assert!(output.out.contains("true"));
+
+        nu!(
+            cwd: dirs.test(),
+            "vol missingdrive out+err>> a"
+        );
+        let output = nu!(cwd: dirs.test(), "(open a | str stats).bytes >= 32");
+        assert!(output.out.contains("true"));
     })
 }
 
@@ -65,6 +90,12 @@ fn redirect_out() {
         );
 
         assert!(output.out.contains("hello"));
+
+        let output = nu!(
+            cwd: dirs.test(),
+            "echo 'hello' out>> a; open a"
+        );
+        assert!(output.out.contains("hellohello"));
     })
 }
 
@@ -124,6 +155,25 @@ fn separate_redirection() {
             let expected_err_file = dirs.test().join("err.txt");
             let actual = file_contents(expected_err_file);
             assert!(actual.contains(expect_body));
+            #[cfg(not(windows))]
+            {
+                sandbox.with_files(vec![FileWithContent("test.sh", script_body)]);
+                nu!(
+                    cwd: dirs.test(),
+                    "bash test.sh out>> out.txt err>> err.txt"
+                );
+                // check for stdout redirection file.
+                let expected_out_file = dirs.test().join("out.txt");
+                let actual = file_contents(expected_out_file);
+                let v: Vec<_> = actual.match_indices("message").collect();
+                assert_eq!(v.len(), 2);
+
+                // check for stderr redirection file.
+                let expected_err_file = dirs.test().join("err.txt");
+                let actual = file_contents(expected_err_file);
+                let v: Vec<_> = actual.match_indices("message").collect();
+                assert_eq!(v.len(), 2);
+            }
         },
     )
 }
@@ -152,6 +202,21 @@ fn same_target_redirection_with_too_much_stderr_not_hang_nushell() {
         let expected_file = dirs.test().join("another_large_file.txt");
         let actual = file_contents(expected_file);
         assert_eq!(actual, format!("{large_file_body}\n"));
+
+        // not hangs in append mode either.
+        let cloned_body = large_file_body.clone();
+        large_file_body.push_str(&format!("\n{cloned_body}"));
+        nu!(
+            cwd: dirs.test(), pipeline(
+                "
+                $env.LARGE = (open --raw a_large_file.txt);
+                nu --testbin echo_env_stderr LARGE out+err>> another_large_file.txt
+                "
+            ),
+        );
+        let expected_file = dirs.test().join("another_large_file.txt");
+        let actual = file_contents(expected_file);
+        assert_eq!(actual, format!("{large_file_body}\n"));
     })
 }
 
@@ -202,6 +267,16 @@ fn redirection_with_pipeline_works() {
             let expected_out_file = dirs.test().join("out.txt");
             let actual = file_contents(expected_out_file);
             assert!(actual.contains(expect_body));
+
+            // check append mode works
+            nu!(
+                cwd: dirs.test(),
+                "bash test.sh o>> out.txt | describe"
+            );
+            let expected_out_file = dirs.test().join("out.txt");
+            let actual = file_contents(expected_out_file);
+            let v: Vec<_> = actual.match_indices("message").collect();
+            assert_eq!(v.len(), 2);
         },
     )
 }
@@ -224,6 +299,22 @@ fn redirect_support_variable() {
         let expected_out_file = dirs.test().join("tmp_file");
         let actual = file_contents(expected_out_file);
         assert!(actual.contains("hello there"));
+
+        // append mode support variable too.
+        let output = nu!(
+            cwd: dirs.test(),
+            "let x = 'tmp_file'; echo 'hello' out>> $x; open tmp_file"
+        );
+        let v: Vec<_> = output.out.match_indices("hello").collect();
+        assert_eq!(v.len(), 2);
+
+        let output = nu!(
+            cwd: dirs.test(),
+            "let x = 'tmp_file'; echo 'hello' out+err>> $x; open tmp_file"
+        );
+        // check for stdout redirection file.
+        let v: Vec<_> = output.out.match_indices("hello").collect();
+        assert_eq!(v.len(), 3);
     })
 }
 
@@ -243,7 +334,7 @@ fn separate_redirection_support_variable() {
                 sandbox.with_files(vec![FileWithContent("test.sh", script_body)]);
                 nu!(
                     cwd: dirs.test(),
-                    r#"let o_f = "out.txt"; let e_f = "err.txt"; bash test.sh out> $o_f err> $e_f"#
+                    r#"let o_f = "out2.txt"; let e_f = "err2.txt"; bash test.sh out> $o_f err> $e_f"#
                 );
             }
             #[cfg(windows)]
@@ -251,18 +342,38 @@ fn separate_redirection_support_variable() {
                 sandbox.with_files(vec![FileWithContent("test.bat", script_body)]);
                 nu!(
                     cwd: dirs.test(),
-                    r#"let o_f = "out.txt"; let e_f = "err.txt"; cmd /D /c test.bat out> $o_f err> $e_f"#
+                    r#"let o_f = "out2.txt"; let e_f = "err2.txt"; cmd /D /c test.bat out> $o_f err> $e_f"#
                 );
             }
             // check for stdout redirection file.
-            let expected_out_file = dirs.test().join("out.txt");
+            let expected_out_file = dirs.test().join("out2.txt");
             let actual = file_contents(expected_out_file);
             assert!(actual.contains(expect_body));
 
             // check for stderr redirection file.
-            let expected_err_file = dirs.test().join("err.txt");
+            let expected_err_file = dirs.test().join("err2.txt");
             let actual = file_contents(expected_err_file);
             assert!(actual.contains(expect_body));
+
+            #[cfg(not(windows))]
+            {
+                sandbox.with_files(vec![FileWithContent("test.sh", script_body)]);
+                nu!(
+                    cwd: dirs.test(),
+                    r#"let o_f = "out2.txt"; let e_f = "err2.txt"; bash test.sh out>> $o_f err>> $e_f"#
+                );
+                // check for stdout redirection file.
+                let expected_out_file = dirs.test().join("out2.txt");
+                let actual = file_contents(expected_out_file);
+                let v: Vec<_> = actual.match_indices("message").collect();
+                assert_eq!(v.len(), 2);
+
+                // check for stderr redirection file.
+                let expected_err_file = dirs.test().join("err2.txt");
+                let actual = file_contents(expected_err_file);
+                let v: Vec<_> = actual.match_indices("message").collect();
+                assert_eq!(v.len(), 2);
+            }
         },
     )
 }
diff --git a/crates/nu-engine/src/eval.rs b/crates/nu-engine/src/eval.rs
index 6bb4cc2130..fed9e451f5 100644
--- a/crates/nu-engine/src/eval.rs
+++ b/crates/nu-engine/src/eval.rs
@@ -7,7 +7,7 @@ use nu_protocol::{
     },
     engine::{Closure, EngineState, Stack},
     DeclId, IntoInterruptiblePipelineData, IntoPipelineData, PipelineData, Range, Record,
-    ShellError, Span, Spanned, Unit, Value, VarId, ENV_VARIABLE_ID,
+    ShellError, Span, Spanned, Type, Unit, Value, VarId, ENV_VARIABLE_ID,
 };
 use std::collections::HashMap;
 use std::thread::{self, JoinHandle};
@@ -754,7 +754,7 @@ fn eval_element_with_input(
             redirect_stdout,
             redirect_stderr,
         ),
-        PipelineElement::Redirection(span, redirection, expr) => {
+        PipelineElement::Redirection(span, redirection, expr, is_append_mode) => {
             match &expr.expr {
                 Expr::String(_)
                 | Expr::FullCellPath(_)
@@ -793,7 +793,11 @@ fn eval_element_with_input(
                     };
 
                     if let Some(save_command) = engine_state.find_decl(b"save", &[]) {
-                        let save_call = gen_save_call(save_command, (*span, expr.clone()), None);
+                        let save_call = gen_save_call(
+                            save_command,
+                            (*span, expr.clone(), *is_append_mode),
+                            None,
+                        );
                         match out_stream {
                             None => {
                                 eval_call(engine_state, stack, &save_call, input).map(|_| {
@@ -847,8 +851,8 @@ fn eval_element_with_input(
             }
         }
         PipelineElement::SeparateRedirection {
-            out: (out_span, out_expr),
-            err: (err_span, err_expr),
+            out: (out_span, out_expr, out_append_mode),
+            err: (err_span, err_expr, err_append_mode),
         } => match (&out_expr.expr, &err_expr.expr) {
             (
                 Expr::String(_)
@@ -867,8 +871,8 @@ fn eval_element_with_input(
                     };
                     let save_call = gen_save_call(
                         save_command,
-                        (*out_span, out_expr.clone()),
-                        Some((*err_span, err_expr.clone())),
+                        (*out_span, out_expr.clone(), *out_append_mode),
+                        Some((*err_span, err_expr.clone(), *err_append_mode)),
                     );
 
                     eval_call(engine_state, stack, &save_call, input).map(|_| {
@@ -901,7 +905,7 @@ fn eval_element_with_input(
         },
         PipelineElement::SameTargetRedirection {
             cmd: (cmd_span, cmd_exp),
-            redirection: (redirect_span, redirect_exp),
+            redirection: (redirect_span, redirect_exp, is_append_mode),
         } => {
             // general idea: eval cmd and call save command to redirect stdout to result.
             input = match &cmd_exp.expr {
@@ -939,6 +943,7 @@ fn eval_element_with_input(
                     *redirect_span,
                     Redirection::Stdout,
                     redirect_exp.clone(),
+                    *is_append_mode,
                 ),
                 input,
                 redirect_stdout,
@@ -1021,8 +1026,8 @@ pub fn eval_block(
                 let next_element = &elements[idx + 1];
                 if matches!(
                     next_element,
-                    PipelineElement::Redirection(_, Redirection::Stderr, _)
-                        | PipelineElement::Redirection(_, Redirection::StdoutAndStderr, _)
+                    PipelineElement::Redirection(_, Redirection::Stderr, _, _)
+                        | PipelineElement::Redirection(_, Redirection::StdoutAndStderr, _, _)
                         | PipelineElement::SeparateRedirection { .. }
                 ) {
                     redirect_stderr = true;
@@ -1033,12 +1038,12 @@ pub fn eval_block(
                 let next_element = &elements[idx + 1];
                 match next_element {
                     // is next element a stdout relative redirection?
-                    PipelineElement::Redirection(_, Redirection::Stdout, _)
-                    | PipelineElement::Redirection(_, Redirection::StdoutAndStderr, _)
+                    PipelineElement::Redirection(_, Redirection::Stdout, _, _)
+                    | PipelineElement::Redirection(_, Redirection::StdoutAndStderr, _, _)
                     | PipelineElement::SeparateRedirection { .. }
                     | PipelineElement::Expression(..) => redirect_stdout = true,
 
-                    PipelineElement::Redirection(_, Redirection::Stderr, _) => {
+                    PipelineElement::Redirection(_, Redirection::Stderr, _, _) => {
                         // a stderr redirection, but we still need to check for the next 2nd
                         // element, to handle for the following case:
                         // cat a.txt err> /dev/null | lines
@@ -1199,10 +1204,19 @@ fn compute(size: i64, unit: Unit, span: Span) -> Result<Value, ShellError> {
 
 fn gen_save_call(
     save_decl_id: DeclId,
-    out_info: (Span, Expression),
-    err_info: Option<(Span, Expression)>,
+    out_info: (Span, Expression, bool),
+    err_info: Option<(Span, Expression, bool)>,
 ) -> Call {
-    let (out_span, out_expr) = out_info;
+    let (out_span, out_expr, out_append_mode) = out_info;
+    let mut call = Call {
+        decl_id: save_decl_id,
+        head: out_span,
+        arguments: vec![],
+        redirect_stdout: false,
+        redirect_stderr: false,
+        parser_info: HashMap::new(),
+    };
+
     let mut args = vec![
         Argument::Positional(out_expr),
         Argument::Named((
@@ -1222,7 +1236,18 @@ fn gen_save_call(
             None,
         )),
     ];
-    if let Some((err_span, err_expr)) = err_info {
+    if out_append_mode {
+        call.set_parser_info(
+            "out-append".to_string(),
+            Expression {
+                expr: Expr::Bool(true),
+                span: out_span,
+                ty: Type::Bool,
+                custom_completion: None,
+            },
+        );
+    }
+    if let Some((err_span, err_expr, err_append_mode)) = err_info {
         args.push(Argument::Named((
             Spanned {
                 item: "stderr".into(),
@@ -1230,17 +1255,22 @@ fn gen_save_call(
             },
             None,
             Some(err_expr),
-        )))
+        )));
+        if err_append_mode {
+            call.set_parser_info(
+                "err-append".to_string(),
+                Expression {
+                    expr: Expr::Bool(true),
+                    span: err_span,
+                    ty: Type::Bool,
+                    custom_completion: None,
+                },
+            );
+        }
     }
 
-    Call {
-        decl_id: save_decl_id,
-        head: out_span,
-        arguments: args,
-        redirect_stdout: false,
-        redirect_stderr: false,
-        parser_info: HashMap::new(),
-    }
+    call.arguments.append(&mut args);
+    call
 }
 
 /// A job which saves `PipelineData` to a file in a child thread.
diff --git a/crates/nu-parser/src/flatten.rs b/crates/nu-parser/src/flatten.rs
index b2bf26f46b..a64d2c63b7 100644
--- a/crates/nu-parser/src/flatten.rs
+++ b/crates/nu-parser/src/flatten.rs
@@ -528,14 +528,14 @@ pub fn flatten_pipeline_element(
                 flatten_expression(working_set, expr)
             }
         }
-        PipelineElement::Redirection(span, _, expr) => {
+        PipelineElement::Redirection(span, _, expr, _) => {
             let mut output = vec![(*span, FlatShape::Redirection)];
             output.append(&mut flatten_expression(working_set, expr));
             output
         }
         PipelineElement::SeparateRedirection {
-            out: (out_span, out_expr),
-            err: (err_span, err_expr),
+            out: (out_span, out_expr, _),
+            err: (err_span, err_expr, _),
         } => {
             let mut output = vec![(*out_span, FlatShape::Redirection)];
             output.append(&mut flatten_expression(working_set, out_expr));
@@ -545,7 +545,7 @@ pub fn flatten_pipeline_element(
         }
         PipelineElement::SameTargetRedirection {
             cmd: (cmd_span, cmd_expr),
-            redirection: (redirect_span, redirect_expr),
+            redirection: (redirect_span, redirect_expr, _),
         } => {
             let mut output = if let Some(span) = cmd_span {
                 let mut output = vec![(*span, FlatShape::Pipe)];
diff --git a/crates/nu-parser/src/lex.rs b/crates/nu-parser/src/lex.rs
index 50f0909d3a..9a48f67f4f 100644
--- a/crates/nu-parser/src/lex.rs
+++ b/crates/nu-parser/src/lex.rs
@@ -8,8 +8,11 @@ pub enum TokenContents {
     PipePipe,
     Semicolon,
     OutGreaterThan,
+    OutGreaterGreaterThan,
     ErrGreaterThan,
+    ErrGreaterGreaterThan,
     OutErrGreaterThan,
+    OutErrGreaterGreaterThan,
     Eol,
 }
 
@@ -260,14 +263,26 @@ pub fn lex_item(
             contents: TokenContents::OutGreaterThan,
             span,
         },
+        b"out>>" | b"o>>" => Token {
+            contents: TokenContents::OutGreaterGreaterThan,
+            span,
+        },
         b"err>" | b"e>" => Token {
             contents: TokenContents::ErrGreaterThan,
             span,
         },
+        b"err>>" | b"e>>" => Token {
+            contents: TokenContents::ErrGreaterGreaterThan,
+            span,
+        },
         b"out+err>" | b"err+out>" | b"o+e>" | b"e+o>" => Token {
             contents: TokenContents::OutErrGreaterThan,
             span,
         },
+        b"out+err>>" | b"err+out>>" | b"o+e>>" | b"e+o>>" => Token {
+            contents: TokenContents::OutErrGreaterGreaterThan,
+            span,
+        },
         b"&&" => {
             err = Some(ParseError::ShellAndAnd(span));
             Token {
diff --git a/crates/nu-parser/src/lite_parser.rs b/crates/nu-parser/src/lite_parser.rs
index 116993d50c..e5c22af912 100644
--- a/crates/nu-parser/src/lite_parser.rs
+++ b/crates/nu-parser/src/lite_parser.rs
@@ -37,16 +37,19 @@ impl LiteCommand {
 #[derive(Debug)]
 pub enum LiteElement {
     Command(Option<Span>, LiteCommand),
-    Redirection(Span, Redirection, LiteCommand),
+    // final field indicates if it's in append mode
+    Redirection(Span, Redirection, LiteCommand, bool),
     // SeparateRedirection variant can only be generated by two different Redirection variant
+    // final bool field indicates if it's in append mode
     SeparateRedirection {
-        out: (Span, LiteCommand),
-        err: (Span, LiteCommand),
+        out: (Span, LiteCommand, bool),
+        err: (Span, LiteCommand, bool),
     },
     // SameTargetRedirection variant can only be generated by Command with Redirection::OutAndErr
+    // redirection's final bool field indicates if it's in append mode
     SameTargetRedirection {
         cmd: (Option<Span>, LiteCommand),
-        redirection: (Span, LiteCommand),
+        redirection: (Span, LiteCommand, bool),
     },
 }
 
@@ -72,10 +75,10 @@ impl LitePipeline {
         self.commands.is_empty()
     }
 
-    pub fn exists(&self, new_target: Redirection) -> bool {
+    pub fn exists(&self, new_target: &Redirection) -> bool {
         for cmd in &self.commands {
-            if let LiteElement::Redirection(_, exists_target, _) = cmd {
-                if exists_target == &new_target {
+            if let LiteElement::Redirection(_, exists_target, _, _) = cmd {
+                if exists_target == new_target {
                     return true;
                 }
             }
@@ -121,7 +124,12 @@ impl LiteBlock {
             if let LiteElement::Command(..) = cmd {
                 cmd_index = Some(index);
             }
-            if let LiteElement::Redirection(_span, Redirection::StdoutAndStderr, _target_cmd) = cmd
+            if let LiteElement::Redirection(
+                _span,
+                Redirection::StdoutAndStderr,
+                _target_cmd,
+                _is_append_mode,
+            ) = cmd
             {
                 outerr_index = Some(index);
                 break;
@@ -134,14 +142,14 @@ impl LiteBlock {
             // `outerr_redirect` and `cmd` should always be `LiteElement::Command` and `LiteElement::Redirection`
             if let (
                 LiteElement::Command(cmd_span, lite_cmd),
-                LiteElement::Redirection(span, _, outerr_cmd),
+                LiteElement::Redirection(span, _, outerr_cmd, is_append_mode),
             ) = (cmd, outerr_redirect)
             {
                 pipeline.insert(
                     cmd_index,
                     LiteElement::SameTargetRedirection {
                         cmd: (cmd_span, lite_cmd),
-                        redirection: (span, outerr_cmd),
+                        redirection: (span, outerr_cmd, is_append_mode),
                     },
                 )
             }
@@ -154,7 +162,8 @@ impl LiteBlock {
         let mut stdout_index = None;
         let mut stderr_index = None;
         for (index, cmd) in pipeline.commands.iter().enumerate() {
-            if let LiteElement::Redirection(_span, redirection, _target_cmd) = cmd {
+            if let LiteElement::Redirection(_span, redirection, _target_cmd, _is_append_mode) = cmd
+            {
                 match *redirection {
                     Redirection::Stderr => stderr_index = Some(index),
                     Redirection::Stdout => stdout_index = Some(index),
@@ -178,8 +187,8 @@ impl LiteBlock {
             };
             // `out_redirect` and `err_redirect` should always be `LiteElement::Redirection`
             if let (
-                LiteElement::Redirection(out_span, _, out_command),
-                LiteElement::Redirection(err_span, _, err_command),
+                LiteElement::Redirection(out_span, _, out_command, out_append_mode),
+                LiteElement::Redirection(err_span, _, err_command, err_append_mode),
             ) = (out_redirect, err_redirect)
             {
                 // using insert with specific index to keep original
@@ -187,8 +196,8 @@ impl LiteBlock {
                 pipeline.insert(
                     new_indx,
                     LiteElement::SeparateRedirection {
-                        out: (out_span, out_command),
-                        err: (err_span, err_command),
+                        out: (out_span, out_command, out_append_mode),
+                        err: (err_span, err_command, err_append_mode),
                     },
                 )
             }
@@ -244,8 +253,11 @@ pub fn lite_parse(tokens: &[Token]) -> (LiteBlock, Option<ParseError>) {
                 last_token = TokenContents::Item;
             }
             TokenContents::OutGreaterThan
+            | TokenContents::OutGreaterGreaterThan
             | TokenContents::ErrGreaterThan
-            | TokenContents::OutErrGreaterThan => {
+            | TokenContents::ErrGreaterGreaterThan
+            | TokenContents::OutErrGreaterThan
+            | TokenContents::OutErrGreaterGreaterThan => {
                 if let Some(err) = push_command_to(
                     &mut curr_pipeline,
                     curr_command,
@@ -375,6 +387,18 @@ pub fn lite_parse(tokens: &[Token]) -> (LiteBlock, Option<ParseError>) {
     }
 }
 
+fn get_redirection(connector: TokenContents) -> Option<(Redirection, bool)> {
+    match connector {
+        TokenContents::OutGreaterThan => Some((Redirection::Stdout, false)),
+        TokenContents::OutGreaterGreaterThan => Some((Redirection::Stdout, true)),
+        TokenContents::ErrGreaterThan => Some((Redirection::Stderr, false)),
+        TokenContents::ErrGreaterGreaterThan => Some((Redirection::Stderr, true)),
+        TokenContents::OutErrGreaterThan => Some((Redirection::StdoutAndStderr, false)),
+        TokenContents::OutErrGreaterGreaterThan => Some((Redirection::StdoutAndStderr, true)),
+        _ => None,
+    }
+}
+
 /// push a `command` to `pipeline`
 ///
 /// It will return Some(err) if `command` is empty and we want to push a
@@ -386,24 +410,11 @@ fn push_command_to(
     last_connector_span: Option<Span>,
 ) -> Option<ParseError> {
     if !command.is_empty() {
-        match last_connector {
-            TokenContents::OutGreaterThan => {
+        match get_redirection(last_connector) {
+            Some((redirect, is_append_mode)) => {
                 let span = last_connector_span
                     .expect("internal error: redirection missing span information");
-                if pipeline.exists(Redirection::Stdout) {
-                    return Some(ParseError::LabeledError(
-                        "Redirection can be set only once".into(),
-                        "try to remove one".into(),
-                        span,
-                    ));
-                }
-
-                pipeline.push(LiteElement::Redirection(span, Redirection::Stdout, command));
-            }
-            TokenContents::ErrGreaterThan => {
-                let span = last_connector_span
-                    .expect("internal error: redirection missing span information");
-                if pipeline.exists(Redirection::Stderr) {
+                if pipeline.exists(&redirect) {
                     return Some(ParseError::LabeledError(
                         "Redirection can be set only once".into(),
                         "try to remove one".into(),
@@ -413,32 +424,20 @@ fn push_command_to(
                 pipeline.push(LiteElement::Redirection(
                     last_connector_span
                         .expect("internal error: redirection missing span information"),
-                    Redirection::Stderr,
+                    redirect,
                     command,
-                ));
-            }
-            TokenContents::OutErrGreaterThan => {
-                pipeline.push(LiteElement::Redirection(
-                    last_connector_span
-                        .expect("internal error: redirection missing span information"),
-                    Redirection::StdoutAndStderr,
-                    command,
-                ));
-            }
-            _ => {
-                pipeline.push(LiteElement::Command(last_connector_span, command));
+                    is_append_mode,
+                ))
             }
+            None => pipeline.push(LiteElement::Command(last_connector_span, command)),
         }
         None
+    } else if get_redirection(last_connector).is_some() {
+        Some(ParseError::Expected(
+            "redirection target",
+            last_connector_span.expect("internal error: redirection missing span information"),
+        ))
     } else {
-        match last_connector {
-            TokenContents::OutGreaterThan
-            | TokenContents::ErrGreaterThan
-            | TokenContents::OutErrGreaterThan => Some(ParseError::Expected(
-                "redirection target",
-                last_connector_span.expect("internal error: redirection missing span information"),
-            )),
-            _ => None,
-        }
+        None
     }
 }
diff --git a/crates/nu-parser/src/parse_keywords.rs b/crates/nu-parser/src/parse_keywords.rs
index 0697c90764..b93d3b0f2c 100644
--- a/crates/nu-parser/src/parse_keywords.rs
+++ b/crates/nu-parser/src/parse_keywords.rs
@@ -1846,11 +1846,12 @@ pub fn parse_module_block(
                         }
                     }
                 }
-                LiteElement::Redirection(_, _, command) => {
+                LiteElement::Redirection(_, _, command, _) => {
                     block.pipelines.push(garbage_pipeline(&command.parts))
                 }
                 LiteElement::SeparateRedirection {
-                    out: (_, command), ..
+                    out: (_, command, _),
+                    ..
                 } => block.pipelines.push(garbage_pipeline(&command.parts)),
                 LiteElement::SameTargetRedirection {
                     cmd: (_, command), ..
diff --git a/crates/nu-parser/src/parser.rs b/crates/nu-parser/src/parser.rs
index cf30f46c24..47964c4754 100644
--- a/crates/nu-parser/src/parser.rs
+++ b/crates/nu-parser/src/parser.rs
@@ -1219,8 +1219,11 @@ fn parse_binary_with_base(
                     TokenContents::Pipe
                     | TokenContents::PipePipe
                     | TokenContents::OutGreaterThan
+                    | TokenContents::OutGreaterGreaterThan
                     | TokenContents::ErrGreaterThan
-                    | TokenContents::OutErrGreaterThan => {
+                    | TokenContents::ErrGreaterGreaterThan
+                    | TokenContents::OutErrGreaterThan
+                    | TokenContents::OutErrGreaterGreaterThan => {
                         working_set.error(ParseError::Expected("binary", span));
                         return garbage(span);
                     }
@@ -5362,14 +5365,14 @@ pub fn parse_pipeline(
 
                     PipelineElement::Expression(*span, expr)
                 }
-                LiteElement::Redirection(span, redirection, command) => {
+                LiteElement::Redirection(span, redirection, command, is_append_mode) => {
                     let expr = parse_value(working_set, command.parts[0], &SyntaxShape::Any);
 
-                    PipelineElement::Redirection(*span, redirection.clone(), expr)
+                    PipelineElement::Redirection(*span, redirection.clone(), expr, *is_append_mode)
                 }
                 LiteElement::SeparateRedirection {
-                    out: (out_span, out_command),
-                    err: (err_span, err_command),
+                    out: (out_span, out_command, out_append_mode),
+                    err: (err_span, err_command, err_append_mode),
                 } => {
                     trace!("parsing: pipeline element: separate redirection");
                     let out_expr =
@@ -5379,13 +5382,13 @@ pub fn parse_pipeline(
                         parse_value(working_set, err_command.parts[0], &SyntaxShape::Any);
 
                     PipelineElement::SeparateRedirection {
-                        out: (*out_span, out_expr),
-                        err: (*err_span, err_expr),
+                        out: (*out_span, out_expr, *out_append_mode),
+                        err: (*err_span, err_expr, *err_append_mode),
                     }
                 }
                 LiteElement::SameTargetRedirection {
                     cmd: (cmd_span, command),
-                    redirection: (redirect_span, redirect_command),
+                    redirection: (redirect_span, redirect_command, is_append_mode),
                 } => {
                     trace!("parsing: pipeline element: same target redirection");
                     let expr = parse_expression(working_set, &command.parts, is_subexpression);
@@ -5393,7 +5396,7 @@ pub fn parse_pipeline(
                         parse_value(working_set, redirect_command.parts[0], &SyntaxShape::Any);
                     PipelineElement::SameTargetRedirection {
                         cmd: (*cmd_span, expr),
-                        redirection: (*redirect_span, redirect_expr),
+                        redirection: (*redirect_span, redirect_expr, *is_append_mode),
                     }
                 }
             })
@@ -5417,9 +5420,10 @@ pub fn parse_pipeline(
     } else {
         match &pipeline.commands[0] {
             LiteElement::Command(_, command)
-            | LiteElement::Redirection(_, _, command)
+            | LiteElement::Redirection(_, _, command, _)
             | LiteElement::SeparateRedirection {
-                out: (_, command), ..
+                out: (_, command, _),
+                ..
             } => {
                 let mut pipeline = parse_builtin_commands(working_set, command, is_subexpression);
 
@@ -5477,7 +5481,7 @@ pub fn parse_pipeline(
             }
             LiteElement::SameTargetRedirection {
                 cmd: (span, command),
-                redirection: (redirect_span, redirect_cmd),
+                redirection: (redirect_span, redirect_cmd, is_append_mode),
             } => {
                 trace!("parsing: pipeline element: same target redirection");
                 let expr = parse_expression(working_set, &command.parts, is_subexpression);
@@ -5488,7 +5492,7 @@ pub fn parse_pipeline(
                 Pipeline {
                     elements: vec![PipelineElement::SameTargetRedirection {
                         cmd: (*span, expr),
-                        redirection: (*redirect_span, redirect_expr),
+                        redirection: (*redirect_span, redirect_expr, *is_append_mode),
                     }],
                 }
             }
@@ -5520,9 +5524,10 @@ pub fn parse_block(
         if pipeline.commands.len() == 1 {
             match &pipeline.commands[0] {
                 LiteElement::Command(_, command)
-                | LiteElement::Redirection(_, _, command)
+                | LiteElement::Redirection(_, _, command, _)
                 | LiteElement::SeparateRedirection {
-                    out: (_, command), ..
+                    out: (_, command, _),
+                    ..
                 }
                 | LiteElement::SameTargetRedirection {
                     cmd: (_, command), ..
@@ -5612,14 +5617,14 @@ pub fn discover_captures_in_pipeline_element(
 ) -> Result<(), ParseError> {
     match element {
         PipelineElement::Expression(_, expression)
-        | PipelineElement::Redirection(_, _, expression)
+        | PipelineElement::Redirection(_, _, expression, _)
         | PipelineElement::And(_, expression)
         | PipelineElement::Or(_, expression) => {
             discover_captures_in_expr(working_set, expression, seen, seen_blocks, output)
         }
         PipelineElement::SeparateRedirection {
-            out: (_, out_expr),
-            err: (_, err_expr),
+            out: (_, out_expr, _),
+            err: (_, err_expr, _),
         } => {
             discover_captures_in_expr(working_set, out_expr, seen, seen_blocks, output)?;
             discover_captures_in_expr(working_set, err_expr, seen, seen_blocks, output)?;
@@ -5627,7 +5632,7 @@ pub fn discover_captures_in_pipeline_element(
         }
         PipelineElement::SameTargetRedirection {
             cmd: (_, cmd_expr),
-            redirection: (_, redirect_expr),
+            redirection: (_, redirect_expr, _),
         } => {
             discover_captures_in_expr(working_set, cmd_expr, seen, seen_blocks, output)?;
             discover_captures_in_expr(working_set, redirect_expr, seen, seen_blocks, output)?;
@@ -5934,28 +5939,38 @@ fn wrap_element_with_collect(
         PipelineElement::Expression(span, expression) => {
             PipelineElement::Expression(*span, wrap_expr_with_collect(working_set, expression))
         }
-        PipelineElement::Redirection(span, redirection, expression) => {
+        PipelineElement::Redirection(span, redirection, expression, is_append_mode) => {
             PipelineElement::Redirection(
                 *span,
                 redirection.clone(),
                 wrap_expr_with_collect(working_set, expression),
+                *is_append_mode,
             )
         }
         PipelineElement::SeparateRedirection {
-            out: (out_span, out_exp),
-            err: (err_span, err_exp),
+            out: (out_span, out_exp, out_append_mode),
+            err: (err_span, err_exp, err_append_mode),
         } => PipelineElement::SeparateRedirection {
-            out: (*out_span, wrap_expr_with_collect(working_set, out_exp)),
-            err: (*err_span, wrap_expr_with_collect(working_set, err_exp)),
+            out: (
+                *out_span,
+                wrap_expr_with_collect(working_set, out_exp),
+                *out_append_mode,
+            ),
+            err: (
+                *err_span,
+                wrap_expr_with_collect(working_set, err_exp),
+                *err_append_mode,
+            ),
         },
         PipelineElement::SameTargetRedirection {
             cmd: (cmd_span, cmd_exp),
-            redirection: (redirect_span, redirect_exp),
+            redirection: (redirect_span, redirect_exp, is_append_mode),
         } => PipelineElement::SameTargetRedirection {
             cmd: (*cmd_span, wrap_expr_with_collect(working_set, cmd_exp)),
             redirection: (
                 *redirect_span,
                 wrap_expr_with_collect(working_set, redirect_exp),
+                *is_append_mode,
             ),
         },
         PipelineElement::And(span, expression) => {
diff --git a/crates/nu-protocol/src/ast/block.rs b/crates/nu-protocol/src/ast/block.rs
index 0840cf642c..21b3e77fa7 100644
--- a/crates/nu-protocol/src/ast/block.rs
+++ b/crates/nu-protocol/src/ast/block.rs
@@ -71,7 +71,7 @@ impl Block {
             if let Some(last) = last.elements.last() {
                 match last {
                     PipelineElement::Expression(_, expr) => expr.ty.clone(),
-                    PipelineElement::Redirection(_, _, _) => Type::Any,
+                    PipelineElement::Redirection(_, _, _, _) => Type::Any,
                     PipelineElement::SeparateRedirection { .. } => Type::Any,
                     PipelineElement::SameTargetRedirection { .. } => Type::Any,
                     PipelineElement::And(_, expr) => expr.ty.clone(),
diff --git a/crates/nu-protocol/src/ast/pipeline.rs b/crates/nu-protocol/src/ast/pipeline.rs
index b3a589b1d2..0abb18f107 100644
--- a/crates/nu-protocol/src/ast/pipeline.rs
+++ b/crates/nu-protocol/src/ast/pipeline.rs
@@ -13,14 +13,17 @@ pub enum Redirection {
 #[derive(Debug, Clone, Serialize, Deserialize)]
 pub enum PipelineElement {
     Expression(Option<Span>, Expression),
-    Redirection(Span, Redirection, Expression),
+    // final field indicates if it's in append mode
+    Redirection(Span, Redirection, Expression, bool),
+    // final bool field indicates if it's in append mode
     SeparateRedirection {
-        out: (Span, Expression),
-        err: (Span, Expression),
+        out: (Span, Expression, bool),
+        err: (Span, Expression, bool),
     },
+    // redirection's final bool field indicates if it's in append mode
     SameTargetRedirection {
         cmd: (Option<Span>, Expression),
-        redirection: (Span, Expression),
+        redirection: (Span, Expression, bool),
     },
     And(Span, Expression),
     Or(Span, Expression),
@@ -30,9 +33,9 @@ impl PipelineElement {
     pub fn expression(&self) -> &Expression {
         match self {
             PipelineElement::Expression(_, expression) => expression,
-            PipelineElement::Redirection(_, _, expression) => expression,
+            PipelineElement::Redirection(_, _, expression, _) => expression,
             PipelineElement::SeparateRedirection {
-                out: (_, expression),
+                out: (_, expression, _),
                 ..
             } => expression,
             PipelineElement::SameTargetRedirection {
@@ -52,9 +55,9 @@ impl PipelineElement {
                 ..
             } => expression.span,
             PipelineElement::Expression(Some(span), expression)
-            | PipelineElement::Redirection(span, _, expression)
+            | PipelineElement::Redirection(span, _, expression, _)
             | PipelineElement::SeparateRedirection {
-                out: (span, expression),
+                out: (span, expression, _),
                 ..
             }
             | PipelineElement::And(span, expression)
@@ -71,7 +74,7 @@ impl PipelineElement {
     pub fn has_in_variable(&self, working_set: &StateWorkingSet) -> bool {
         match self {
             PipelineElement::Expression(_, expression)
-            | PipelineElement::Redirection(_, _, expression)
+            | PipelineElement::Redirection(_, _, expression, _)
             | PipelineElement::And(_, expression)
             | PipelineElement::Or(_, expression)
             | PipelineElement::SameTargetRedirection {
@@ -79,8 +82,8 @@ impl PipelineElement {
                 ..
             } => expression.has_in_variable(working_set),
             PipelineElement::SeparateRedirection {
-                out: (_, out_expr),
-                err: (_, err_expr),
+                out: (_, out_expr, _),
+                err: (_, err_expr, _),
             } => out_expr.has_in_variable(working_set) || err_expr.has_in_variable(working_set),
         }
     }
@@ -88,7 +91,7 @@ impl PipelineElement {
     pub fn replace_in_variable(&mut self, working_set: &mut StateWorkingSet, new_var_id: VarId) {
         match self {
             PipelineElement::Expression(_, expression)
-            | PipelineElement::Redirection(_, _, expression)
+            | PipelineElement::Redirection(_, _, expression, _)
             | PipelineElement::And(_, expression)
             | PipelineElement::Or(_, expression)
             | PipelineElement::SameTargetRedirection {
@@ -96,8 +99,8 @@ impl PipelineElement {
                 ..
             } => expression.replace_in_variable(working_set, new_var_id),
             PipelineElement::SeparateRedirection {
-                out: (_, out_expr),
-                err: (_, err_expr),
+                out: (_, out_expr, _),
+                err: (_, err_expr, _),
             } => {
                 if out_expr.has_in_variable(working_set) {
                     out_expr.replace_in_variable(working_set, new_var_id)
@@ -117,7 +120,7 @@ impl PipelineElement {
     ) {
         match self {
             PipelineElement::Expression(_, expression)
-            | PipelineElement::Redirection(_, _, expression)
+            | PipelineElement::Redirection(_, _, expression, _)
             | PipelineElement::And(_, expression)
             | PipelineElement::Or(_, expression)
             | PipelineElement::SameTargetRedirection {
@@ -125,7 +128,7 @@ impl PipelineElement {
                 ..
             }
             | PipelineElement::SeparateRedirection {
-                out: (_, expression),
+                out: (_, expression, _),
                 ..
             } => expression.replace_span(working_set, replaced, new_span),
         }