diff --git a/Cargo.lock b/Cargo.lock
index 1aa3c3416..7a34ad49b 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -543,12 +543,6 @@ version = "2.1.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f4f47ca1860a761136924ddd2422ba77b2ea54fe8cc75b9040804a0d9d32ad97"
 
-[[package]]
-name = "debug_print"
-version = "1.0.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8f215f9b7224f49fb73256115331f677d868b34d18b65dbe4db392e6021eea90"
-
 [[package]]
 name = "diff"
 version = "0.1.12"
@@ -1917,7 +1911,6 @@ version = "0.0.7"
 dependencies = [
  "byte-unit",
  "clap",
- "debug_print",
  "gcd",
  "libc",
  "signal-hook",
diff --git a/src/uu/dd/Cargo.toml b/src/uu/dd/Cargo.toml
index f65d0bf12..da0165245 100644
--- a/src/uu/dd/Cargo.toml
+++ b/src/uu/dd/Cargo.toml
@@ -17,7 +17,6 @@ path = "src/dd.rs"
 [dependencies]
 byte-unit = "4.0"
 clap = { version = "2.33", features = [ "wrap_help" ] }
-debug_print = "1.0"
 gcd = "2.0"
 libc = "0.2"
 signal-hook = "0.3.9"
diff --git a/src/uu/dd/cspell.json b/src/uu/dd/cspell.json
index fb29630b2..4e47b090f 100644
--- a/src/uu/dd/cspell.json
+++ b/src/uu/dd/cspell.json
@@ -17,7 +17,9 @@
         "fullblock",
         "noxfer",
         "iflag",
+        "iflags",
         "oflag",
+        "oflags",
         "infile",
         "outfile",
         "fileio",
@@ -33,9 +35,30 @@
         "datastructures",
         "creat",
         "mult",
-        "unfailed",
         "behaviour",
         "ctty",
+        "noatime",
+        "fname",
+        "fileout",
+        "ofile",
+        "doesnt",
+        "parseargs",
+        "rlen",
+        "wlen",
+        "rstat",
+        "wstat",
+        "rposition",
+        "btotal",
+        "sigval",
+        "sigusr",
+        "rmax",
+        "rsofar",
+        "rremain",
+        "bremain",
+        "oconvflags",
+        "fpath",
+        "testfile",
+        "specfile"
     ],
     "ignorePaths": [
         "**/test-resources/*.test",
diff --git a/src/uu/dd/src/dd.rs b/src/uu/dd/src/dd.rs
index 717c9d88b..d0faaacf7 100644
--- a/src/uu/dd/src/dd.rs
+++ b/src/uu/dd/src/dd.rs
@@ -24,6 +24,7 @@ use conversion_tables::*;
 use byte_unit::Byte;
 use clap::{self, crate_version};
 use gcd::Gcd;
+#[cfg(target_os = "linux")]
 use signal_hook::consts::signal;
 use std::cmp;
 use std::convert::TryInto;
@@ -34,7 +35,9 @@ use std::io::{self, Read, Seek, Write};
 #[cfg(target_os = "linux")]
 use std::os::unix::fs::OpenOptionsExt;
 use std::path::Path;
-use std::sync::{atomic::AtomicUsize, atomic::Ordering, mpsc, Arc};
+#[cfg(target_os = "linux")]
+use std::sync::atomic::Ordering;
+use std::sync::{atomic::AtomicUsize, mpsc, Arc};
 use std::thread;
 use std::time;
 
@@ -168,15 +171,15 @@ impl Input<File> {
 impl<R: Read> Read for Input<R> {
     fn read(&mut self, buf: &mut [u8]) -> io::Result<usize> {
         let mut base_idx = 0;
-        let tlen = buf.len();
+        let target_len = buf.len();
         loop {
             match self.src.read(&mut buf[base_idx..]) {
                 Ok(0) => return Ok(base_idx),
                 Ok(rlen) if self.iflags.fullblock => {
                     base_idx += rlen;
 
-                    if base_idx >= tlen {
-                        return Ok(tlen);
+                    if base_idx >= target_len {
+                        return Ok(target_len);
                     }
                 }
                 Ok(len) => return Ok(len),
@@ -707,6 +710,7 @@ fn gen_prog_updater(rx: mpsc::Receiver<ProgUpdate>, print_level: Option<StatusLe
     #[cfg(target_os = "linux")]
     const SIGUSR1_USIZE: usize = signal::SIGUSR1 as usize;
     // --------------------------------------------------------------
+    #[cfg(target_os = "linux")]
     fn posixly_correct() -> bool {
         env::var("POSIXLY_CORRECT").is_ok()
     }
@@ -731,21 +735,11 @@ fn gen_prog_updater(rx: mpsc::Receiver<ProgUpdate>, print_level: Option<StatusLe
             }
         });
 
-        loop {
-            // Wait for update
-            let update = match (rx.recv(), print_level) {
-                (Ok(update), Some(StatusLevel::Progress)) => {
-                    reprint_prog_line(&update);
-
-                    update
-                }
-                (Ok(update), _) => update,
-                (Err(_), _) => {
-                    // recv only fails permanently, so we break here to
-                    // avoid recv'ing on a broken pipe
-                    break;
-                }
-            };
+        while let Ok(update) = rx.recv() {
+            // (Re)print status line if progress is requested.
+            if Some(StatusLevel::Progress) == print_level {
+                reprint_prog_line(&update);
+            }
             // Handle signals
             #[cfg(target_os = "linux")]
             if let SIGUSR1_USIZE = sigval.load(Ordering::Relaxed) {
diff --git a/src/uu/dd/src/dd_unit_tests/block_unblock_tests.rs b/src/uu/dd/src/dd_unit_tests/block_unblock_tests.rs
index 1b9698638..ca633906e 100644
--- a/src/uu/dd/src/dd_unit_tests/block_unblock_tests.rs
+++ b/src/uu/dd/src/dd_unit_tests/block_unblock_tests.rs
@@ -15,19 +15,15 @@ macro_rules! make_block_test (
                             print_level: None,
                             count: None,
                             cflags: IConvFlags {
-                                ctable: None,
                                 block: $block,
-                                unblock: None,
-                                swab: false,
-                                sync: None,
-                                noerror: false,
+                                ..IConvFlags::default()
                             },
-                            iflags: DEFAULT_IFLAGS,
+                            iflags: IFlags::default(),
                         },
                         Output {
                             dst: File::create(format!("./test-resources/FAILED-{}.test", $test_name)).unwrap(),
                             obs: 512,
-                            cflags: DEFAULT_CFO,
+                            cflags: OConvFlags::default(),
                         },
                         $spec,
                         format!("./test-resources/FAILED-{}.test", $test_name)
@@ -47,19 +43,15 @@ macro_rules! make_unblock_test (
                             print_level: None,
                             count: None,
                             cflags: IConvFlags {
-                                ctable: None,
-                                block: None,
                                 unblock: $unblock,
-                                swab: false,
-                                sync: None,
-                                noerror: false,
+                                ..IConvFlags::default()
                             },
-                            iflags: DEFAULT_IFLAGS,
+                            iflags: IFlags::default(),
                         },
                         Output {
                             dst: File::create(format!("./test-resources/FAILED-{}.test", $test_name)).unwrap(),
                             obs: 512,
-                            cflags: DEFAULT_CFO,
+                            cflags: OConvFlags::default(),
                         },
                         $spec,
                         format!("./test-resources/FAILED-{}.test", $test_name)
@@ -247,7 +239,11 @@ fn block_test_double_surrounded_nl_double_trunc() {
 make_block_test!(
     block_cbs16,
     "block-cbs-16",
-    File::open("./test-resources/dd-block-cbs16.test").unwrap(),
+    if cfg!(unix) {
+        File::open("./test-resources/dd-block-cbs16.test").unwrap()
+    } else {
+        File::open("./test-resources/dd-block-cbs16-win.test").unwrap()
+    },
     Some(16),
     File::open("./test-resources/dd-block-cbs16.spec").unwrap()
 );
@@ -255,7 +251,11 @@ make_block_test!(
 make_block_test!(
     block_cbs16_as_cbs8,
     "block-cbs-16-as-cbs8",
-    File::open("./test-resources/dd-block-cbs16.test").unwrap(),
+    if cfg!(unix) {
+        File::open("./test-resources/dd-block-cbs16.test").unwrap()
+    } else {
+        File::open("./test-resources/dd-block-cbs16-win.test").unwrap()
+    },
     Some(8),
     File::open("./test-resources/dd-block-cbs8.spec").unwrap()
 );
@@ -263,7 +263,11 @@ make_block_test!(
 make_block_test!(
     block_consecutive_nl,
     "block-consecutive-nl",
-    File::open("./test-resources/dd-block-consecutive-nl.test").unwrap(),
+    if cfg!(unix) {
+        File::open("./test-resources/dd-block-consecutive-nl.test").unwrap()
+    } else {
+        File::open("./test-resources/dd-block-consecutive-nl-win.test").unwrap()
+    },
     Some(16),
     File::open("./test-resources/dd-block-consecutive-nl-cbs16.spec").unwrap()
 );
@@ -335,7 +339,11 @@ make_unblock_test!(
     "unblock-multi-16",
     File::open("./test-resources/dd-unblock-cbs16.test").unwrap(),
     Some(16),
-    File::open("./test-resources/dd-unblock-cbs16.spec").unwrap()
+    if cfg!(unix) {
+        File::open("./test-resources/dd-unblock-cbs16.spec").unwrap()
+    } else {
+        File::open("./test-resources/dd-unblock-cbs16-win.spec").unwrap()
+    }
 );
 
 make_unblock_test!(
@@ -343,5 +351,9 @@ make_unblock_test!(
     "unblock-multi-16-as-8",
     File::open("./test-resources/dd-unblock-cbs16.test").unwrap(),
     Some(8),
-    File::open("./test-resources/dd-unblock-cbs8.spec").unwrap()
+    if cfg!(unix) {
+        File::open("./test-resources/dd-unblock-cbs8.spec").unwrap()
+    } else {
+        File::open("./test-resources/dd-unblock-cbs8-win.spec").unwrap()
+    }
 );
diff --git a/src/uu/dd/src/dd_unit_tests/conv_sync_tests.rs b/src/uu/dd/src/dd_unit_tests/conv_sync_tests.rs
index 8563985c6..945fbe7af 100644
--- a/src/uu/dd/src/dd_unit_tests/conv_sync_tests.rs
+++ b/src/uu/dd/src/dd_unit_tests/conv_sync_tests.rs
@@ -12,19 +12,15 @@ macro_rules! make_sync_test (
                             print_level: None,
                             count: None,
                             cflags: IConvFlags {
-                                ctable: None,
-                                block: None,
-                                unblock: None,
-                                swab: false,
                                 sync: $sync,
-                                noerror: false,
+                                ..IConvFlags::default()
                             },
-                            iflags: DEFAULT_IFLAGS,
+                            iflags: IFlags::default(),
                         },
                         Output {
                             dst: File::create(format!("./test-resources/FAILED-{}.test", $test_name)).unwrap(),
                             obs: $obs,
-                            cflags: DEFAULT_CFO,
+                            cflags: OConvFlags::default(),
                         },
                         $spec,
                         format!("./test-resources/FAILED-{}.test", $test_name)
diff --git a/src/uu/dd/src/dd_unit_tests/conversion_tests.rs b/src/uu/dd/src/dd_unit_tests/conversion_tests.rs
index 5276f38b3..d3a9229b6 100644
--- a/src/uu/dd/src/dd_unit_tests/conversion_tests.rs
+++ b/src/uu/dd/src/dd_unit_tests/conversion_tests.rs
@@ -12,12 +12,12 @@ macro_rules! make_conv_test (
                             print_level: None,
                             count: None,
                             cflags: icf!($ctable),
-                            iflags: DEFAULT_IFLAGS,
+                            iflags: IFlags::default(),
                         },
                         Output {
                             dst: File::create(format!("./test-resources/FAILED-{}.test", $test_name)).unwrap(),
                             obs: 512,
-                            cflags: DEFAULT_CFO,
+                            cflags: OConvFlags::default(),
                         },
                         $spec,
                         format!("./test-resources/FAILED-{}.test", $test_name)
@@ -37,12 +37,12 @@ macro_rules! make_icf_test (
                             print_level: None,
                             count: None,
                             cflags: $icf,
-                            iflags: DEFAULT_IFLAGS,
+                            iflags: IFlags::default(),
                         },
                         Output {
                             dst: File::create(format!("./test-resources/FAILED-{}.test", $test_name)).unwrap(),
                             obs: 512,
-                            cflags: DEFAULT_CFO,
+                            cflags: OConvFlags::default(),
                         },
                         $spec,
                         format!("./test-resources/FAILED-{}.test", $test_name)
@@ -142,13 +142,13 @@ fn all_valid_ascii_ebcdic_ascii_roundtrip_conv_test() {
         print_level: None,
         count: None,
         cflags: icf!(Some(&ASCII_TO_EBCDIC)),
-        iflags: DEFAULT_IFLAGS,
+        iflags: IFlags::default(),
     };
 
     let o = Output {
         dst: File::create(&tmp_fname_ae).unwrap(),
         obs: 1024,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     };
 
     dd_fileout(i, o).unwrap();
@@ -164,13 +164,13 @@ fn all_valid_ascii_ebcdic_ascii_roundtrip_conv_test() {
         print_level: None,
         count: None,
         cflags: icf!(Some(&EBCDIC_TO_ASCII)),
-        iflags: DEFAULT_IFLAGS,
+        iflags: IFlags::default(),
     };
 
     let o = Output {
         dst: File::create(&tmp_fname_ea).unwrap(),
         obs: 1024,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     };
 
     dd_fileout(i, o).unwrap();
diff --git a/src/uu/dd/src/dd_unit_tests/mod.rs b/src/uu/dd/src/dd_unit_tests/mod.rs
index fc8836e11..90ef00eaf 100644
--- a/src/uu/dd/src/dd_unit_tests/mod.rs
+++ b/src/uu/dd/src/dd_unit_tests/mod.rs
@@ -9,34 +9,6 @@ use std::fs;
 use std::io::prelude::*;
 use std::io::BufReader;
 
-const DEFAULT_CFO: OConvFlags = OConvFlags {
-    sparse: false,
-    excl: false,
-    nocreat: false,
-    notrunc: false,
-    fdatasync: false,
-    fsync: false,
-};
-
-const DEFAULT_IFLAGS: IFlags = IFlags {
-    cio: false,
-    direct: false,
-    directory: false,
-    dsync: false,
-    sync: false,
-    nocache: false,
-    nonblock: false,
-    noatime: false,
-    noctty: false,
-    nofollow: false,
-    nolinks: false,
-    binary: false,
-    text: false,
-    fullblock: false,
-    count_bytes: false,
-    skip_bytes: false,
-};
-
 struct LazyReader<R: Read> {
     src: R,
 }
@@ -50,19 +22,11 @@ impl<R: Read> Read for LazyReader<R> {
 
 #[macro_export]
 macro_rules! icf (
-    () =>
-    {
-        icf!(None)
-    };
     ( $ctable:expr ) =>
     {
         IConvFlags {
             ctable: $ctable,
-            block: None,
-            unblock: None,
-            swab: false,
-            sync: None,
-            noerror: false,
+            ..IConvFlags::default()
         }
     };
 );
@@ -84,13 +48,13 @@ macro_rules! make_spec_test (
                             ibs: 512,
                             print_level: None,
                             count: None,
-                            cflags: icf!(),
-                            iflags: DEFAULT_IFLAGS,
+                            cflags: IConvFlags::default(),
+                            iflags: IFlags::default(),
                         },
                         Output {
                             dst: File::create(format!("./test-resources/FAILED-{}.test", $test_name)).unwrap(),
                             obs: 512,
-                            cflags: DEFAULT_CFO,
+                            cflags: OConvFlags::default(),
                         },
                         $spec,
                         format!("./test-resources/FAILED-{}.test", $test_name)
diff --git a/src/uu/dd/src/dd_unit_tests/sanity_tests.rs b/src/uu/dd/src/dd_unit_tests/sanity_tests.rs
index fff942d26..1d0276cb3 100644
--- a/src/uu/dd/src/dd_unit_tests/sanity_tests.rs
+++ b/src/uu/dd/src/dd_unit_tests/sanity_tests.rs
@@ -52,13 +52,13 @@ make_io_test!(
         ibs: 521,
         print_level: None,
         count: None,
-        cflags: icf!(),
-        iflags: DEFAULT_IFLAGS,
+        cflags: IConvFlags::default(),
+        iflags: IFlags::default(),
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 1031,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/random-5828891cb1230748e146f34223bbd3b5.test").unwrap()
 );
@@ -72,13 +72,13 @@ make_io_test!(
         ibs: 1031,
         print_level: None,
         count: None,
-        cflags: icf!(),
-        iflags: DEFAULT_IFLAGS,
+        cflags: IConvFlags::default(),
+        iflags: IFlags::default(),
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 521,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/random-5828891cb1230748e146f34223bbd3b5.test").unwrap()
 );
@@ -92,13 +92,13 @@ make_io_test!(
         ibs: 1024,
         print_level: None,
         count: Some(CountType::Reads(32)),
-        cflags: icf!(),
-        iflags: DEFAULT_IFLAGS,
+        cflags: IConvFlags::default(),
+        iflags: IFlags::default(),
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 1024,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/deadbeef-18d99661a1de1fc9af21b0ec2cd67ba3.test").unwrap()
 );
@@ -112,13 +112,13 @@ make_io_test!(
         ibs: 531,
         print_level: None,
         count: Some(CountType::Bytes(32 * 1024)),
-        cflags: icf!(),
-        iflags: DEFAULT_IFLAGS,
+        cflags: IConvFlags::default(),
+        iflags: IFlags::default(),
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 1031,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/deadbeef-18d99661a1de1fc9af21b0ec2cd67ba3.test").unwrap()
 );
@@ -132,13 +132,13 @@ make_io_test!(
         ibs: 1024,
         print_level: None,
         count: Some(CountType::Reads(16)),
-        cflags: icf!(),
-        iflags: DEFAULT_IFLAGS,
+        cflags: IConvFlags::default(),
+        iflags: IFlags::default(),
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 1031,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/gnudd-deadbeef-first-16k.spec").unwrap()
 );
@@ -152,13 +152,13 @@ make_io_test!(
         ibs: 531,
         print_level: None,
         count: Some(CountType::Bytes(12345)),
-        cflags: icf!(),
-        iflags: DEFAULT_IFLAGS,
+        cflags: IConvFlags::default(),
+        iflags: IFlags::default(),
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 1031,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/gnudd-deadbeef-first-12345.spec").unwrap()
 );
@@ -172,13 +172,13 @@ make_io_test!(
         ibs: 1024,
         print_level: None,
         count: Some(CountType::Reads(32)),
-        cflags: icf!(),
-        iflags: DEFAULT_IFLAGS,
+        cflags: IConvFlags::default(),
+        iflags: IFlags::default(),
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 1024,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/gnudd-random-first-32k.spec").unwrap()
 );
@@ -192,13 +192,13 @@ make_io_test!(
         ibs: 521,
         print_level: None,
         count: Some(CountType::Bytes(32 * 1024)),
-        cflags: icf!(),
-        iflags: DEFAULT_IFLAGS,
+        cflags: IConvFlags::default(),
+        iflags: IFlags::default(),
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 1031,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/gnudd-random-first-32k.spec").unwrap()
 );
@@ -215,30 +215,16 @@ make_io_test!(
         ibs: 521,
         print_level: None,
         count: None,
-        cflags: icf!(),
+        cflags: IConvFlags::default(),
         iflags: IFlags {
             fullblock: true,
-            cio: false,
-            direct: false,
-            directory: false,
-            dsync: false,
-            sync: false,
-            nocache: false,
-            nonblock: false,
-            noatime: false,
-            noctty: false,
-            nofollow: false,
-            nolinks: false,
-            binary: false,
-            text: false,
-            count_bytes: false,
-            skip_bytes: false,
+            ..IFlags::default()
         },
     },
     Output {
         dst: DST_PLACEHOLDER,
         obs: 1031,
-        cflags: DEFAULT_CFO,
+        cflags: OConvFlags::default(),
     },
     File::open("./test-resources/random-5828891cb1230748e146f34223bbd3b5.test").unwrap()
 );
@@ -316,7 +302,7 @@ fn bsize_test_bs_eq() {
 
 #[test]
 #[should_panic]
-fn test_nocreate_causes_failure_when_ofile_doesnt_exist() {
+fn test_nocreat_causes_failure_when_ofile_doesnt_exist() {
     let args = vec![
         String::from("dd"),
         String::from("--conv=nocreat"),
diff --git a/src/uu/dd/src/parseargs.rs b/src/uu/dd/src/parseargs.rs
index c0e22c520..a27ab3cb0 100644
--- a/src/uu/dd/src/parseargs.rs
+++ b/src/uu/dd/src/parseargs.rs
@@ -186,7 +186,7 @@ impl std::str::FromStr for Flag {
             "direct" =>
             // Ok(Self::Direct),
             {
-                if cfg!(unix) {
+                if cfg!(target_os = "linux") {
                     Ok(Self::Direct)
                 } else {
                     Err(ParseError::Unimplemented(s.to_string()))
@@ -195,7 +195,7 @@ impl std::str::FromStr for Flag {
             "directory" =>
             // Ok(Self::Directory),
             {
-                if cfg!(unix) {
+                if cfg!(target_os = "linux") {
                     Ok(Self::Directory)
                 } else {
                     Err(ParseError::Unimplemented(s.to_string()))
@@ -204,7 +204,7 @@ impl std::str::FromStr for Flag {
             "dsync" =>
             // Ok(Self::Dsync),
             {
-                if cfg!(unix) {
+                if cfg!(target_os = "linux") {
                     Ok(Self::Dsync)
                 } else {
                     Err(ParseError::Unimplemented(s.to_string()))
@@ -213,7 +213,7 @@ impl std::str::FromStr for Flag {
             "sync" =>
             // Ok(Self::Sync),
             {
-                if cfg!(unix) {
+                if cfg!(target_os = "linux") {
                     Ok(Self::Sync)
                 } else {
                     Err(ParseError::Unimplemented(s.to_string()))
@@ -227,7 +227,7 @@ impl std::str::FromStr for Flag {
             "nonblock" =>
             // Ok(Self::NonBlock),
             {
-                if cfg!(unix) {
+                if cfg!(target_os = "linux") {
                     Ok(Self::NonBlock)
                 } else {
                     Err(ParseError::Unimplemented(s.to_string()))
@@ -236,7 +236,7 @@ impl std::str::FromStr for Flag {
             "noatime" =>
             // Ok(Self::NoATime),
             {
-                if cfg!(unix) {
+                if cfg!(target_os = "linux") {
                     Ok(Self::NoATime)
                 } else {
                     Err(ParseError::Unimplemented(s.to_string()))
@@ -245,7 +245,7 @@ impl std::str::FromStr for Flag {
             "noctty" =>
             // Ok(Self::NoCtty),
             {
-                if cfg!(unix) {
+                if cfg!(target_os = "linux") {
                     Ok(Self::NoCtty)
                 } else {
                     Err(ParseError::Unimplemented(s.to_string()))
@@ -254,7 +254,7 @@ impl std::str::FromStr for Flag {
             "nofollow" =>
             // Ok(Self::NoFollow),
             {
-                if cfg!(unix) {
+                if cfg!(target_os = "linux") {
                     Ok(Self::NoFollow)
                 } else {
                     Err(ParseError::Unimplemented(s.to_string()))
@@ -421,16 +421,13 @@ fn parse_flag_list<T: std::str::FromStr<Err = ParseError>>(
 /// Parse Conversion Options (Input Variety)
 /// Construct and validate a IConvFlags
 pub fn parse_conv_flag_input(matches: &Matches) -> Result<IConvFlags, ParseError> {
-    let flags = parse_flag_list("conv", matches)?;
-    let cbs = parse_cbs(matches)?;
-
+    let mut iconvflags = IConvFlags::default();
     let mut fmt = None;
     let mut case = None;
-    let mut block = None;
-    let mut unblock = None;
-    let mut swab = false;
-    let mut sync = false;
-    let mut noerror = false;
+    let mut is_sync = false;
+
+    let flags = parse_flag_list(options::CONV, matches)?;
+    let cbs = parse_cbs(matches)?;
 
     for flag in flags {
         match flag {
@@ -469,27 +466,36 @@ pub fn parse_conv_flag_input(matches: &Matches) -> Result<IConvFlags, ParseError
                     case = Some(flag)
                 }
             }
-            ConvFlag::Block => match (cbs, unblock) {
-                (Some(cbs), None) => block = Some(cbs),
+            ConvFlag::Block => match (cbs, iconvflags.unblock) {
+                (Some(cbs), None) => iconvflags.block = Some(cbs),
                 (None, _) => return Err(ParseError::BlockUnblockWithoutCBS),
                 (_, Some(_)) => return Err(ParseError::MultipleBlockUnblock),
             },
-            ConvFlag::Unblock => match (cbs, block) {
-                (Some(cbs), None) => unblock = Some(cbs),
+            ConvFlag::Unblock => match (cbs, iconvflags.block) {
+                (Some(cbs), None) => iconvflags.unblock = Some(cbs),
                 (None, _) => return Err(ParseError::BlockUnblockWithoutCBS),
                 (_, Some(_)) => return Err(ParseError::MultipleBlockUnblock),
             },
-            ConvFlag::Swab => swab = true,
-            ConvFlag::Sync => sync = true,
-            ConvFlag::NoError => noerror = true,
+            ConvFlag::Swab => iconvflags.swab = true,
+            ConvFlag::Sync => is_sync = true,
+            ConvFlag::NoError => iconvflags.noerror = true,
             _ => {}
         }
     }
 
+    // The final conversion table depends on both
+    // fmt (eg. ASCII -> EBCDIC)
+    // case (eg. UCASE -> LCASE)
+    // So the final value can't be set until all flags are parsed.
     let ctable = parse_ctable(fmt, case);
-    let sync = if sync && (block.is_some() || unblock.is_some()) {
+
+    // The final value of sync depends on block/unblock
+    // block implies sync with ' '
+    // unblock implies sync with 0
+    // So the final value can't be set until all flags are parsed.
+    let sync = if is_sync && (iconvflags.block.is_some() || iconvflags.unblock.is_some()) {
         Some(b' ')
-    } else if sync {
+    } else if is_sync {
         Some(0u8)
     } else {
         None
@@ -497,27 +503,17 @@ pub fn parse_conv_flag_input(matches: &Matches) -> Result<IConvFlags, ParseError
 
     Ok(IConvFlags {
         ctable,
-        block,
-        unblock,
-        swab,
         sync,
-        noerror,
+        ..iconvflags
     })
 }
 
 /// Parse Conversion Options (Output Variety)
 /// Construct and validate a OConvFlags
 pub fn parse_conv_flag_output(matches: &Matches) -> Result<OConvFlags, ParseError> {
-    let flags = parse_flag_list(options::CONV, matches)?;
+    let mut oconvflags = OConvFlags::default();
 
-    let mut oconvflags = OConvFlags {
-        sparse: false,
-        excl: false,
-        nocreat: false,
-        notrunc: false,
-        fdatasync: false,
-        fsync: false,
-    };
+    let flags = parse_flag_list(options::CONV, matches)?;
 
     for flag in flags {
         match flag {
@@ -548,24 +544,7 @@ pub fn parse_conv_flag_output(matches: &Matches) -> Result<OConvFlags, ParseErro
 
 /// Parse IFlags struct from CL-input
 pub fn parse_iflags(matches: &Matches) -> Result<IFlags, ParseError> {
-    let mut iflags = IFlags {
-        cio: false,
-        direct: false,
-        directory: false,
-        dsync: false,
-        sync: false,
-        nocache: false,
-        nonblock: false,
-        noatime: false,
-        noctty: false,
-        nofollow: false,
-        nolinks: false,
-        binary: false,
-        text: false,
-        fullblock: false,
-        count_bytes: false,
-        skip_bytes: false,
-    };
+    let mut iflags = IFlags::default();
 
     let flags = parse_flag_list(options::IFLAG, matches)?;
 
@@ -596,23 +575,7 @@ pub fn parse_iflags(matches: &Matches) -> Result<IFlags, ParseError> {
 
 /// Parse OFlags struct from CL-input
 pub fn parse_oflags(matches: &Matches) -> Result<OFlags, ParseError> {
-    let mut oflags = OFlags {
-        append: false,
-        cio: false,
-        direct: false,
-        directory: false,
-        dsync: false,
-        sync: false,
-        nocache: false,
-        nonblock: false,
-        noatime: false,
-        noctty: false,
-        nofollow: false,
-        nolinks: false,
-        binary: false,
-        text: false,
-        seek_bytes: false,
-    };
+    let mut oflags = OFlags::default();
 
     let flags = parse_flag_list(options::OFLAG, matches)?;
 
diff --git a/src/uu/dd/src/parseargs/unit_tests.rs b/src/uu/dd/src/parseargs/unit_tests.rs
index 60b027bb6..765eb6f46 100644
--- a/src/uu/dd/src/parseargs/unit_tests.rs
+++ b/src/uu/dd/src/parseargs/unit_tests.rs
@@ -4,7 +4,7 @@ use crate::StatusLevel;
 
 #[cfg(not(target_os = "linux"))]
 #[test]
-fn unimplemented_flags_should_error_non_unix() {
+fn unimplemented_flags_should_error_non_linux() {
     let mut succeeded = Vec::new();
 
     // The following flags are only implemented in linux
@@ -518,29 +518,35 @@ test_byte_parser!(test_bytes_GB, "3GB", 3 * 1000 * 1000 * 1000);
 test_byte_parser!(test_bytes_G, "3G", 3 * 1024 * 1024 * 1024);
 test_byte_parser!(test_bytes_Gi, "3GiB", 3 * 1024 * 1024 * 1024);
 
-test_byte_parser!(test_bytes_TB, "4TB", 4 * 1000 * 1000 * 1000 * 1000);
-test_byte_parser!(test_bytes_T, "4T", 4 * 1024 * 1024 * 1024 * 1024);
-test_byte_parser!(test_bytes_Ti, "4TiB", 4 * 1024 * 1024 * 1024 * 1024);
+#[cfg(target_pointer_width = "64")]
+#[cfg(test)]
+mod test_64bit_arch {
+    use super::*;
 
-test_byte_parser!(test_bytes_PB, "5PB", 5 * 1000 * 1000 * 1000 * 1000 * 1000);
-test_byte_parser!(test_bytes_P, "5P", 5 * 1024 * 1024 * 1024 * 1024 * 1024);
-test_byte_parser!(test_bytes_Pi, "5PiB", 5 * 1024 * 1024 * 1024 * 1024 * 1024);
+    test_byte_parser!(test_bytes_TB, "4TB", 4 * 1000 * 1000 * 1000 * 1000);
+    test_byte_parser!(test_bytes_T, "4T", 4 * 1024 * 1024 * 1024 * 1024);
+    test_byte_parser!(test_bytes_Ti, "4TiB", 4 * 1024 * 1024 * 1024 * 1024);
 
-test_byte_parser!(
-    test_bytes_EB,
-    "6EB",
-    6 * 1000 * 1000 * 1000 * 1000 * 1000 * 1000
-);
-test_byte_parser!(
-    test_bytes_E,
-    "6E",
-    6 * 1024 * 1024 * 1024 * 1024 * 1024 * 1024
-);
-test_byte_parser!(
-    test_bytes_Ei,
-    "6EiB",
-    6 * 1024 * 1024 * 1024 * 1024 * 1024 * 1024
-);
+    test_byte_parser!(test_bytes_PB, "5PB", 5 * 1000 * 1000 * 1000 * 1000 * 1000);
+    test_byte_parser!(test_bytes_P, "5P", 5 * 1024 * 1024 * 1024 * 1024 * 1024);
+    test_byte_parser!(test_bytes_Pi, "5PiB", 5 * 1024 * 1024 * 1024 * 1024 * 1024);
+
+    test_byte_parser!(
+        test_bytes_EB,
+        "6EB",
+        6 * 1000 * 1000 * 1000 * 1000 * 1000 * 1000
+    );
+    test_byte_parser!(
+        test_bytes_E,
+        "6E",
+        6 * 1024 * 1024 * 1024 * 1024 * 1024 * 1024
+    );
+    test_byte_parser!(
+        test_bytes_Ei,
+        "6EiB",
+        6 * 1024 * 1024 * 1024 * 1024 * 1024 * 1024
+    );
+}
 
 #[test]
 #[should_panic]
diff --git a/src/uu/dd/test-resources/dd-block-cbs16-win.test b/src/uu/dd/test-resources/dd-block-cbs16-win.test
new file mode 100644
index 000000000..9b51cb8f3
--- /dev/null
+++ b/src/uu/dd/test-resources/dd-block-cbs16-win.test
@@ -0,0 +1,16 @@
+0
+01
+012
+0123
+01234
+012345
+0123456
+01234567
+012345678
+0123456789
+0123456789a
+0123456789ab
+0123456789abc
+0123456789abcd
+0123456789abcde
+0123456789abcdef
diff --git a/src/uu/dd/test-resources/dd-block-consecutive-nl-win.test b/src/uu/dd/test-resources/dd-block-consecutive-nl-win.test
new file mode 100644
index 000000000..1bf473b2b
--- /dev/null
+++ b/src/uu/dd/test-resources/dd-block-consecutive-nl-win.test
@@ -0,0 +1,4 @@
+pre
+
+
+post
diff --git a/src/uu/dd/test-resources/dd-unblock-cbs16-win.spec b/src/uu/dd/test-resources/dd-unblock-cbs16-win.spec
new file mode 100644
index 000000000..9b51cb8f3
--- /dev/null
+++ b/src/uu/dd/test-resources/dd-unblock-cbs16-win.spec
@@ -0,0 +1,16 @@
+0
+01
+012
+0123
+01234
+012345
+0123456
+01234567
+012345678
+0123456789
+0123456789a
+0123456789ab
+0123456789abc
+0123456789abcd
+0123456789abcde
+0123456789abcdef
diff --git a/src/uu/dd/test-resources/dd-unblock-cbs8-win.spec b/src/uu/dd/test-resources/dd-unblock-cbs8-win.spec
new file mode 100644
index 000000000..8031036c1
--- /dev/null
+++ b/src/uu/dd/test-resources/dd-unblock-cbs8-win.spec
@@ -0,0 +1,32 @@
+0
+
+01
+
+012
+
+0123
+
+01234
+
+012345
+
+0123456
+
+01234567
+
+01234567
+8
+01234567
+89
+01234567
+89a
+01234567
+89ab
+01234567
+89abc
+01234567
+89abcd
+01234567
+89abcde
+01234567
+89abcdef
diff --git a/tests/by-util/test_dd.rs b/tests/by-util/test_dd.rs
index a601190d9..e038ee24b 100644
--- a/tests/by-util/test_dd.rs
+++ b/tests/by-util/test_dd.rs
@@ -213,27 +213,12 @@ fn test_excl_causes_failure_when_present() {
         .fails();
 }
 
-#[cfg(target_os = "linux")]
-#[test]
-fn test_atime_updated() {
-    let fname = "this-file-exists-no-noatime.txt";
-    assert_fixture_exists!(&fname);
-
-    let (fix, mut ucmd) = at_and_ucmd!();
-    ucmd.args(&["status=none", inf!(fname)]);
-
-    let pre_atime = fix.metadata(fname).accessed().unwrap();
-
-    ucmd.pipe_in("").run().no_stderr().success();
-    std::thread::sleep(std::time::Duration::from_millis(10));
-
-    let post_atime = fix.metadata(fname).accessed().unwrap();
-    assert!(pre_atime != post_atime);
-}
-
 #[cfg(target_os = "linux")]
 #[test]
 fn test_noatime_does_not_update_infile_atime() {
+    // NOTE: Not all environments support tracking access time. If this
+    // test fails on some systems and passes on others, assume the functionality
+    // is not working and the systems that pass it simply don't update file access time.
     let fname = "this-ifile-exists-noatime.txt";
     assert_fixture_exists!(&fname);
 
@@ -251,6 +236,9 @@ fn test_noatime_does_not_update_infile_atime() {
 #[cfg(target_os = "linux")]
 #[test]
 fn test_noatime_does_not_update_ofile_atime() {
+    // NOTE: Not all environments support tracking access time. If this
+    // test fails on some systems and passes on others, assume the functionality
+    // is not working and the systems that pass it simply don't update file access time.
     let fname = "this-ofile-exists-noatime.txt";
     assert_fixture_exists!(&fname);
 
diff --git a/tests/fixtures/dd/cspell.json b/tests/fixtures/dd/cspell.json
index 19986ad83..65fa927d6 100644
--- a/tests/fixtures/dd/cspell.json
+++ b/tests/fixtures/dd/cspell.json
@@ -1,6 +1,29 @@
 {
     "version": "0.1",
     "language": "en",
+    "words": [
+        "fname",
+        "fpath",
+        "specfile",
+        "testfile",
+        "iflag",
+        "iflags",
+        "oflag",
+        "oflags",
+        "noxfer",
+        "nocreat",
+        "noatime",
+        "infile",
+        "outfile",
+        "unspec",
+        "fullblock",
+        "urand",
+        "tname",
+        "fileio",
+        "gibi",
+        "ucase",
+        "lcase"
+    ],
     "ignorePaths": [
         "*.txt",
         "*.spec"