diff --git a/lib/core/libimagrt/src/logger.rs b/lib/core/libimagrt/src/logger.rs
index 3090fb3f..ef586bbb 100644
--- a/lib/core/libimagrt/src/logger.rs
+++ b/lib/core/libimagrt/src/logger.rs
@@ -370,6 +370,7 @@ fn aggregate_module_settings(_matches: &ArgMatches, config: Option<&Value>)
                 for (module_name, v) in t {
                     let destinations = inner_try! {
                         v.read("destinations")
+                            .context("Failed reading header 'destinations'")
                             .map_err(Error::from)
                             .context(EM::TomlQueryError)?
                             .map(|val| {
@@ -384,6 +385,7 @@ fn aggregate_module_settings(_matches: &ArgMatches, config: Option<&Value>)
 
                     let level = inner_try! {
                         v.read_string("level")
+                            .context("Failed reading header 'level'")
                             .map_err(Error::from)
                             .context(EM::TomlQueryError)?
                             .map(|s| match_log_level_str(&s))
diff --git a/lib/core/libimagrt/src/runtime.rs b/lib/core/libimagrt/src/runtime.rs
index a4cba80f..58321938 100644
--- a/lib/core/libimagrt/src/runtime.rs
+++ b/lib/core/libimagrt/src/runtime.rs
@@ -408,6 +408,7 @@ impl<'a> Runtime<'a> {
 
             let mut buf = String::new();
             lock.read_to_string(&mut buf)
+                .context("Failed to read stdin to buffer")
                 .map_err(Error::from)
                 .and_then(|_| {
                     trace!("Got IDs = {}", buf);
diff --git a/lib/core/libimagstore/src/configuration.rs b/lib/core/libimagstore/src/configuration.rs
index d0b3452d..3b9cc1e8 100644
--- a/lib/core/libimagstore/src/configuration.rs
+++ b/lib/core/libimagstore/src/configuration.rs
@@ -34,6 +34,7 @@ pub fn config_implicit_store_create_allowed(config: &Option<Value>) -> Result<bo
 
     if let Some(ref t) = *config {
         t.read_bool(key)
+            .context(format_err!("Error reading header '{}' in configuration", key))
             .map_err(Error::from)
             .context(EM::TomlQueryError)?
             .ok_or_else(|| format_err!("Config key missing: {}", key))
diff --git a/lib/core/libimagstore/src/storeid.rs b/lib/core/libimagstore/src/storeid.rs
index 2c504f2c..c1853652 100644
--- a/lib/core/libimagstore/src/storeid.rs
+++ b/lib/core/libimagstore/src/storeid.rs
@@ -184,6 +184,9 @@ impl<'a> StoreIdWithBase<'a> {
                store_part.display());
         let p = full_path
             .strip_prefix(store_part)
+            .context(format_err!("Cannot strip prefix '{}' from path: '{}'",
+                                 store_part.display(),
+                                 full_path.display()))
             .map_err(Error::from)
             .context(err_msg("Error building Store Id from full path"))?;
         Ok(StoreIdWithBase(store_part, PathBuf::from(p)))
diff --git a/lib/domain/libimagbookmark/src/collection.rs b/lib/domain/libimagbookmark/src/collection.rs
index 9d2dd1e3..19f10f64 100644
--- a/lib/domain/libimagbookmark/src/collection.rs
+++ b/lib/domain/libimagbookmark/src/collection.rs
@@ -27,6 +27,7 @@
 use regex::Regex;
 
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::Error;
 
 use libimagstore::store::Store;
@@ -52,19 +53,28 @@ impl<'a> BookmarkCollectionStore<'a> for Store {
 
     fn new(&'a self, name: &str) -> Result<FileLockEntry<'a>> {
         crate::module_path::new_id(name)
-            .and_then(|id| self.create(id).map_err(Error::from))
+            .and_then(|id| self.create(id)
+                      .context("Failed to create FileLockEntry")
+                      .map_err(Error::from))
+            .context("Failed to create Id for new Bookmark Collection")
             .map_err(Error::from)
     }
 
     fn get(&'a self, name: &str) -> Result<Option<FileLockEntry<'a>>> {
         crate::module_path::new_id(name)
-            .and_then(|id| self.get(id).map_err(Error::from))
+            .and_then(|id| self.get(id)
+                      .context("Failed to get FileLockEntry")
+                      .map_err(Error::from))
+            .context("Failed to get Bookmark Collection")
             .map_err(Error::from)
     }
 
     fn delete(&'a self, name: &str) -> Result<()> {
         crate::module_path::new_id(name)
-            .and_then(|id| self.delete(id).map_err(Error::from))
+            .and_then(|id| self.delete(id)
+                      .context("Failed to delete FileLockEntry")
+                      .map_err(Error::from))
+            .context("Failed to delete Bookmark Collection")
             .map_err(Error::from)
     }
 
diff --git a/lib/domain/libimagcontact/src/iter.rs b/lib/domain/libimagcontact/src/iter.rs
index ea836d55..9335882c 100644
--- a/lib/domain/libimagcontact/src/iter.rs
+++ b/lib/domain/libimagcontact/src/iter.rs
@@ -25,6 +25,7 @@ use libimagerror::errors::ErrorMsg as EM;
 use crate::contact::Contact;
 use failure::Fallible as Result;
 use failure::Error;
+use failure::ResultExt;
 
 pub struct ContactIter<'a>(StoreIdIterator, &'a Store);
 
@@ -44,12 +45,21 @@ impl<'a> Iterator for ContactIter<'a> {
         loop {
             match self.0.next() {
                 None          => return None,
-                Some(Err(e))  => return Some(Err(e).map_err(Error::from)),
+                Some(Err(e))  => {
+                    let e = Err(e)
+                        .context("Found error while iterating over contacts")
+                        .map_err(Error::from);
+
+                    return Some(e)
+                },
                 Some(Ok(sid)) => match self.1.get(sid.clone()).map_err(From::from) {
                     Err(e)          => return Some(Err(e)),
                     Ok(None)        => return
                         Some(Err(Error::from(EM::EntryNotFound(sid.local_display_string())))),
-                    Ok(Some(entry)) => match entry.is_contact().map_err(Error::from) {
+                    Ok(Some(entry)) => match entry.is_contact()
+                        .context("Cannot check whether entry is a contact")
+                        .map_err(Error::from)
+                    {
                         Ok(true)    => return Some(Ok(entry)),
                         Ok(false)   => continue,
                         Err(e)      => return Some(Err(e)),
diff --git a/lib/domain/libimagcontact/src/store.rs b/lib/domain/libimagcontact/src/store.rs
index 351365b4..66c76469 100644
--- a/lib/domain/libimagcontact/src/store.rs
+++ b/lib/domain/libimagcontact/src/store.rs
@@ -27,6 +27,7 @@ use toml_query::insert::TomlValueInsertExt;
 use vobject::vcard::Vcard;
 use failure::Error;
 use failure::Fallible as Result;
+use failure::ResultExt;
 
 use libimagstore::storeid::StoreId;
 use libimagstore::iter::Entries;
@@ -152,7 +153,7 @@ impl<'a> ContactStore<'a> for Store {
 ///
 /// That means calculating the StoreId and the Value from the vcard data
 fn prepare_fetching_from_store(buf: &str) -> Result<(StoreId, Value)> {
-    let vcard = Vcard::build(&buf).map_err(Error::from)?;
+    let vcard = Vcard::build(&buf).context("Cannot parse Vcard").map_err(Error::from)?;
     debug!("Parsed: {:?}", vcard);
 
     let uid = vcard.uid()
diff --git a/lib/domain/libimagdiary/src/diary.rs b/lib/domain/libimagdiary/src/diary.rs
index 0c447df5..b268b0b6 100644
--- a/lib/domain/libimagdiary/src/diary.rs
+++ b/lib/domain/libimagdiary/src/diary.rs
@@ -30,6 +30,7 @@ use itertools::Itertools;
 use chrono::naive::NaiveDateTime;
 use chrono::Timelike;
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::Error;
 
 use crate::entry::IsDiaryEntry;
@@ -141,6 +142,7 @@ impl Diary for Store {
     fn diary_names(&self) -> Result<DiaryNameIterator> {
         self.entries()
             .map(|it| DiaryNameIterator::new(it.into_storeid_iter()))
+            .context("Failed building DiaryNameIteator from entries iterator")
             .map_err(Error::from)
     }
 
diff --git a/lib/domain/libimagdiary/src/diaryid.rs b/lib/domain/libimagdiary/src/diaryid.rs
index bdf94447..c28aebdd 100644
--- a/lib/domain/libimagdiary/src/diaryid.rs
+++ b/lib/domain/libimagdiary/src/diaryid.rs
@@ -234,6 +234,7 @@ impl FromStoreId for DiaryId {
         let day: Result<u32> = next_component(&mut cmps)
             .and_then(|s| {
                 s.parse::<u32>()
+                    .context("Failed to parse day from u32")
                     .map_err(Error::from)
                     .context(err_msg("ID parse error"))
                     .map_err(Error::from)
@@ -242,6 +243,7 @@ impl FromStoreId for DiaryId {
         let month: Result<u32> = next_component(&mut cmps)
             .and_then(|s| {
                 s.parse::<u32>()
+                    .context("Failed to parse month from u32")
                     .map_err(Error::from)
                     .context(err_msg("ID Parse error"))
                     .map_err(Error::from)
@@ -250,6 +252,7 @@ impl FromStoreId for DiaryId {
         let year: Result<i32> = next_component(&mut cmps)
             .and_then(|s| {
                 s.parse::<i32>()
+                    .context("Failed to parse year from i32")
                     .map_err(Error::from)
                     .context(err_msg("ID Parse error"))
                     .map_err(Error::from)
diff --git a/lib/domain/libimaghabit/src/habit.rs b/lib/domain/libimaghabit/src/habit.rs
index 2e99a443..7041dff7 100644
--- a/lib/domain/libimaghabit/src/habit.rs
+++ b/lib/domain/libimaghabit/src/habit.rs
@@ -25,6 +25,7 @@ use chrono::Local;
 use chrono::NaiveDate;
 use failure::Error;
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::err_msg;
 
 use crate::iter::HabitInstanceStoreIdIterator;
@@ -257,7 +258,9 @@ impl HabitTemplate for Entry {
 }
 
 fn instance_id_for_name_and_datestr(habit_name: &String, habit_date: &String) -> Result<StoreId> {
-    crate::module_path::new_id(format!("instance/{}-{}", habit_name, habit_date)).map_err(Error::from)
+    crate::module_path::new_id(format!("instance/{}-{}", habit_name, habit_date))
+        .context(format_err!("Failed building ID for instance: habit name = {}, habit date = {}", habit_name, habit_date))
+        .map_err(Error::from)
 }
 
 pub mod builder {
diff --git a/lib/domain/libimaghabit/src/iter.rs b/lib/domain/libimaghabit/src/iter.rs
index f58dbd56..3344e9a8 100644
--- a/lib/domain/libimaghabit/src/iter.rs
+++ b/lib/domain/libimaghabit/src/iter.rs
@@ -19,6 +19,7 @@
 
 use failure::Error;
 use failure::Fallible as Result;
+use failure::ResultExt;
 
 use libimagstore::storeid::StoreIdIterator;
 use libimagstore::storeid::StoreIdIteratorWithStore;
@@ -33,11 +34,11 @@ impl Iterator for HabitTemplateStoreIdIterator {
 
     fn next(&mut self) -> Option<Self::Item> {
         while let Some(n) = self.0.next() {
-            match n {
+            match n.context("Error while iterating").map_err(Error::from) {
                 Ok(n) => if n.is_habit_template() {
                     return Some(Ok(n))
                 },
-                Err(e) => return Some(Err(e).map_err(Error::from)),
+                Err(e) => return Some(Err(e)),
             }
         }
         None
diff --git a/lib/domain/libimaghabit/src/util.rs b/lib/domain/libimaghabit/src/util.rs
index 51adb6c1..bfe99374 100644
--- a/lib/domain/libimaghabit/src/util.rs
+++ b/lib/domain/libimaghabit/src/util.rs
@@ -21,6 +21,7 @@ use std::ops::BitXor;
 
 use failure::Error;
 use failure::Fallible as Result;
+use failure::ResultExt;
 
 use crate::habit::HabitTemplate;
 use crate::instance::HabitInstance;
@@ -88,6 +89,7 @@ pub fn get_string_header_from_entry(e: &Entry, path: &'static str) -> Result<Str
     e.get_header()
         .read_string(path)?
         .ok_or_else(|| EM::EntryHeaderFieldMissing(path))
+        .context(format_err!("Error while reading header '{}' from '{}'", path, e.get_location()))
         .map_err(Error::from)
 }
 
diff --git a/lib/domain/libimaglog/src/log.rs b/lib/domain/libimaglog/src/log.rs
index 78901cda..5855e744 100644
--- a/lib/domain/libimaglog/src/log.rs
+++ b/lib/domain/libimaglog/src/log.rs
@@ -24,6 +24,7 @@ use libimagentryutil::isa::IsKindHeaderPathProvider;
 
 use failure::Fallible as Result;
 use failure::Error;
+use failure::ResultExt;
 
 
 use toml::Value;
@@ -38,12 +39,13 @@ provide_kindflag_path!(pub IsLog, "log.is_log");
 
 impl Log for Entry {
     fn is_log(&self) -> Result<bool> {
-        self.is::<IsLog>().map_err(From::from)
+        self.is::<IsLog>().context("Cannot check whether Entry is a Log").map_err(From::from)
     }
 
     fn make_log_entry(&mut self) -> Result<()> {
         self.get_header_mut()
             .insert("log.is_log", Value::Boolean(true))
+            .context("Cannot insert 'log.is_log' into header of entry")
             .map_err(Error::from)
             .map(|_| ())
     }
diff --git a/lib/domain/libimagmail/src/mail.rs b/lib/domain/libimagmail/src/mail.rs
index fca352b7..5da48580 100644
--- a/lib/domain/libimagmail/src/mail.rs
+++ b/lib/domain/libimagmail/src/mail.rs
@@ -57,12 +57,17 @@ impl Mail for Entry {
             .context(format_err!("Cannot parse Email {}", mail_file_location.display()))?
             .headers
             .into_iter()
-            .filter_map(|hdr| match hdr.get_key() {
-                Err(e) => Some(Err(e).map_err(Error::from)),
-                Ok(k) => if k == field {
-                    Some(Ok(hdr))
-                } else {
-                    None
+            .filter_map(|hdr| {
+                match hdr.get_key()
+                    .context(format_err!("Cannot fetch key '{}' from Email {}", field, mail_file_location.display()))
+                    .map_err(Error::from)
+                {
+                    Ok(k) => if k == field {
+                        Some(Ok(hdr))
+                    } else {
+                        None
+                    },
+                    Err(e) => Some(Err(e)),
                 }
             })
             .next()
@@ -135,12 +140,17 @@ impl<'a> MailHeader<'a> {
     pub fn get_field(&self, field: &str) -> Result<Option<String>> {
         match self.0
             .iter()
-            .filter_map(|hdr| match hdr.get_key() {
-                Err(e) => Some(Err(e).map_err(Error::from)),
-                Ok(key) => if key == field {
-                    Some(Ok(hdr))
-                } else {
-                    None
+            .filter_map(|hdr| {
+                match hdr.get_key()
+                    .context(format_err!("Cannot get field {}", field))
+                    .map_err(Error::from)
+                {
+                    Ok(key) => if key == field {
+                        Some(Ok(hdr))
+                    } else {
+                        None
+                    },
+                    Err(e) => Some(Err(e))
                 }
             })
             .next()
diff --git a/lib/domain/libimagmail/src/util.rs b/lib/domain/libimagmail/src/util.rs
index c4c3c91f..4be9a786 100644
--- a/lib/domain/libimagmail/src/util.rs
+++ b/lib/domain/libimagmail/src/util.rs
@@ -39,8 +39,7 @@ pub(crate) fn get_message_header_at_key<P: AsRef<Path>, K: AsRef<str>>(p: P, k:
         .context(format_err!("Cannot parse Email {}", p.as_ref().display()))?
         .headers
         .into_iter()
-        .filter_map(|hdr| match hdr.get_key() {
-            Err(e) => Some(Err(e).map_err(Error::from)),
+        .filter_map(|hdr| match hdr.get_key().context("Cannot get key from mail header").map_err(Error::from) {
             Ok(key) => {
                 let lower_key = key.to_lowercase();
                 trace!("Test: {} == {}", lower_key, k.as_ref());
@@ -49,11 +48,12 @@ pub(crate) fn get_message_header_at_key<P: AsRef<Path>, K: AsRef<str>>(p: P, k:
                 } else {
                     None
                 }
-            }
+            },
+            Err(e) => Some(Err(e))
         })
         .next()
         .ok_or_else(|| format_err!("'{}' not found in {}", k.as_ref(), p.as_ref().display()))?
-        .and_then(|hdr| hdr.get_value().map_err(Error::from))
+        .and_then(|hdr| hdr.get_value().context("Cannot get value from mail header").map_err(Error::from))
 }
 
 pub(crate) fn get_message_id_for_mailfile<P: AsRef<Path>>(p: P) -> Result<String> {
@@ -77,6 +77,7 @@ pub fn get_mail_text_content<P: AsRef<Path>>(p: P) -> Result<String> {
     ::mailparse::parse_mail(::std::fs::read_to_string(p.as_ref())?.as_bytes())
         .context(format_err!("Cannot parse Email {}", p.as_ref().display()))?
         .get_body()
+        .context("Cannot get body of mail")
         .map_err(Error::from)
 }
 
diff --git a/lib/domain/libimagnotes/src/iter.rs b/lib/domain/libimagnotes/src/iter.rs
index 74908c8f..3dc2047e 100644
--- a/lib/domain/libimagnotes/src/iter.rs
+++ b/lib/domain/libimagnotes/src/iter.rs
@@ -23,6 +23,7 @@ use libimagstore::storeid::StoreIdIterator;
 use crate::notestoreid::*;
 use failure::Fallible as Result;
 use failure::Error;
+use failure::ResultExt;
 
 #[derive(Debug)]
 pub struct NoteIterator(StoreIdIterator);
@@ -40,11 +41,11 @@ impl Iterator for NoteIterator {
 
     fn next(&mut self) -> Option<Self::Item> {
         while let Some(n) = self.0.next() {
-            match n {
+            match n.context("Error while iterating").map_err(Error::from) {
                 Ok(n) => if n.is_note_id() {
                     return Some(Ok(n));
                 },
-                Err(e) => return Some(Err(e).map_err(Error::from)),
+                Err(e) => return Some(Err(e)),
             }
         }
 
diff --git a/lib/domain/libimagnotes/src/note.rs b/lib/domain/libimagnotes/src/note.rs
index 2a55ce2b..15a0142f 100644
--- a/lib/domain/libimagnotes/src/note.rs
+++ b/lib/domain/libimagnotes/src/note.rs
@@ -27,6 +27,7 @@ use toml_query::set::TomlValueSetExt;
 
 use failure::Fallible as Result;
 use failure::Error;
+use failure::ResultExt;
 
 pub trait Note {
     fn set_name(&mut self, n: String) -> Result<()>;
@@ -40,6 +41,7 @@ impl Note for Entry {
     fn set_name(&mut self, n: String) -> Result<()> {
         self.get_header_mut()
             .set("note.name", Value::String(n))
+            .context(format_err!("Cannot set 'note.name' in header of {}", self.get_location()))
             .map_err(Error::from)
             .map(|_| ())
     }
diff --git a/lib/domain/libimagtimetrack/src/iter/create.rs b/lib/domain/libimagtimetrack/src/iter/create.rs
index 82519036..d08fc253 100644
--- a/lib/domain/libimagtimetrack/src/iter/create.rs
+++ b/lib/domain/libimagtimetrack/src/iter/create.rs
@@ -21,6 +21,7 @@ use toml::Value;
 use toml_query::insert::TomlValueInsertExt;
 use chrono::naive::NaiveDateTime as NDT;
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::Error;
 
 use crate::constants::*;
@@ -60,6 +61,7 @@ impl<'a> Iterator for CreateTimeTrackIter<'a>
                 res.and_then(|(id, starttime)| {
                     self.store
                         .create(id)
+                        .context("Failed to create entry")
                         .map_err(Error::from)
                         .and_then(|mut entry| {
                             let v = Value::String(starttime.format(DATE_TIME_FORMAT).to_string());
diff --git a/lib/domain/libimagtimetrack/src/timetracking.rs b/lib/domain/libimagtimetrack/src/timetracking.rs
index 045725f2..f47be7f7 100644
--- a/lib/domain/libimagtimetrack/src/timetracking.rs
+++ b/lib/domain/libimagtimetrack/src/timetracking.rs
@@ -37,6 +37,7 @@ use toml_query::delete::TomlValueDeleteExt;
 use toml_query::insert::TomlValueInsertExt;
 use toml_query::read::TomlValueReadTypeExt;
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::Error;
 
 pub trait TimeTracking {
@@ -64,6 +65,8 @@ impl TimeTracking for Entry {
     fn get_timetrack_tag(&self) -> Result<TTT> {
         self.get_header()
             .read_string(DATE_TIME_TAG_HEADER_PATH)
+            .context(format_err!("Failed to read header '{}' of {}", DATE_TIME_TAG_HEADER_PATH,
+                                 self.get_location()))
             .map_err(Error::from)?
             .ok_or_else(|| Error::from(EM::EntryHeaderReadError))
             .map(Into::into)
@@ -74,6 +77,8 @@ impl TimeTracking for Entry {
 
         self.get_header_mut()
             .insert(DATE_TIME_START_HEADER_PATH, Value::String(s))
+            .context(format_err!("Failed get header '{}' of {}", DATE_TIME_START_HEADER_PATH,
+                                 self.get_location()))
             .map_err(Error::from)
             .map(|_| ())
     }
@@ -81,6 +86,8 @@ impl TimeTracking for Entry {
     fn get_start_datetime(&self) -> Result<Option<NaiveDateTime>> {
         self.get_header()
             .read_string(DATE_TIME_START_HEADER_PATH)
+            .context(format_err!("Failed read header '{}' of {}", DATE_TIME_START_HEADER_PATH,
+                                 self.get_location()))
             .map_err(Error::from)
             .and_then(header_value_to_dt)
     }
@@ -88,6 +95,8 @@ impl TimeTracking for Entry {
     fn delete_start_datetime(&mut self) -> Result<()> {
         self.get_header_mut()
             .delete(DATE_TIME_START_HEADER_PATH)
+            .context(format_err!("Failed delete header '{}' of {}", DATE_TIME_START_HEADER_PATH,
+                                 self.get_location()))
             .map_err(Error::from)
             .map(|_| ())
     }
@@ -97,6 +106,8 @@ impl TimeTracking for Entry {
 
         self.get_header_mut()
             .insert(DATE_TIME_END_HEADER_PATH, Value::String(s))
+            .context(format_err!("Failed insert header '{}' in {}", DATE_TIME_END_HEADER_PATH,
+                                 self.get_location()))
             .map_err(Error::from)
             .map(|_| ())
     }
@@ -104,6 +115,8 @@ impl TimeTracking for Entry {
     fn get_end_datetime(&self) -> Result<Option<NaiveDateTime>> {
         self.get_header()
             .read_string(DATE_TIME_END_HEADER_PATH)
+            .context(format_err!("Failed read header '{}' of {}", DATE_TIME_END_HEADER_PATH,
+                                 self.get_location()))
             .map_err(Error::from)
             .and_then(header_value_to_dt)
     }
@@ -111,6 +124,8 @@ impl TimeTracking for Entry {
     fn delete_end_datetime(&mut self) -> Result<()> {
         self.get_header_mut()
             .delete(DATE_TIME_END_HEADER_PATH)
+            .context(format_err!("Failed delete header '{}' of {}", DATE_TIME_END_HEADER_PATH,
+                                 self.get_location()))
             .map_err(Error::from)
             .map(|_| ())
     }
@@ -135,7 +150,10 @@ impl TimeTracking for Entry {
 
 fn header_value_to_dt(val: Option<String>) -> Result<Option<NaiveDateTime>> {
     match val {
-        Some(ref s) => NaiveDateTime::parse_from_str(s, DATE_TIME_FORMAT).map_err(Error::from).map(Some),
+        Some(ref s) => NaiveDateTime::parse_from_str(s, DATE_TIME_FORMAT)
+            .context(format_err!("Failed to parse '{}' datetime with format '{}'",
+                                 s, DATE_TIME_FORMAT))
+            .map_err(Error::from).map(Some),
         None => Ok(None),
     }
 }
diff --git a/lib/domain/libimagtimetrack/src/timetrackingstore.rs b/lib/domain/libimagtimetrack/src/timetrackingstore.rs
index 2144185b..967c8958 100644
--- a/lib/domain/libimagtimetrack/src/timetrackingstore.rs
+++ b/lib/domain/libimagtimetrack/src/timetrackingstore.rs
@@ -26,6 +26,7 @@ use chrono::NaiveDateTime as NDT;
 use toml::Value;
 use toml_query::insert::TomlValueInsertExt;
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::Error;
 
 use libimagstore::store::Store;
@@ -70,6 +71,8 @@ impl<'a> TimeTrackStore<'a> for Store {
         use std::path::PathBuf;
 
         COMPILER.compile(CRATE_NAME, start)
+            .context(format_err!("Failed to compile DatePath for crate '{}' with start = '{}'",
+                                 CRATE_NAME, start))
             .map_err(Error::from)
             .map(|mut id| {
                 id.local_push(PathBuf::from(ts.as_str()));
diff --git a/lib/domain/libimagwiki/src/wiki.rs b/lib/domain/libimagwiki/src/wiki.rs
index 6e88a760..4024e29a 100644
--- a/lib/domain/libimagwiki/src/wiki.rs
+++ b/lib/domain/libimagwiki/src/wiki.rs
@@ -27,6 +27,7 @@ use libimagentrylink::internal::InternalLinker;
 use failure::Fallible as Result;
 use failure::Error;
 use failure::err_msg;
+use failure::ResultExt;
 
 pub struct Wiki<'a, 'b>(&'a Store, &'b str);
 
@@ -58,6 +59,7 @@ impl<'a, 'b> Wiki<'a, 'b> {
 
         self.0
             .get(sid)
+            .context("Cannot get ID from store")
             .map_err(Error::from)?
             .ok_or_else(|| Error::from(err_msg("Missing index")))
     }
diff --git a/lib/entry/libimagentrycategory/src/category.rs b/lib/entry/libimagentrycategory/src/category.rs
index de81bfbd..fb7268a7 100644
--- a/lib/entry/libimagentrycategory/src/category.rs
+++ b/lib/entry/libimagentrycategory/src/category.rs
@@ -27,6 +27,7 @@ use libimagentrylink::internal::InternalLinker;
 use toml_query::read::TomlValueReadTypeExt;
 
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::Error;
 use failure::err_msg;
 use crate::store::CATEGORY_REGISTER_NAME_FIELD_PATH;
@@ -49,6 +50,7 @@ impl Category for Entry {
         trace!("Getting category name of '{:?}'", self.get_location());
         self.get_header()
             .read_string(CATEGORY_REGISTER_NAME_FIELD_PATH)
+            .context(format_err!("Failed to read header at '{}'", CATEGORY_REGISTER_NAME_FIELD_PATH))
             .map_err(Error::from)?
             .ok_or_else(|| Error::from(err_msg("Category name missing")))
     }
diff --git a/lib/entry/libimagentrycategory/src/entry.rs b/lib/entry/libimagentrycategory/src/entry.rs
index 8260de8a..9876add4 100644
--- a/lib/entry/libimagentrycategory/src/entry.rs
+++ b/lib/entry/libimagentrycategory/src/entry.rs
@@ -52,7 +52,7 @@ impl EntryCategory for Entry {
         trace!("Setting category '{}' UNCHECKED", s);
         self.get_header_mut()
             .insert(&String::from("category.value"), Value::String(s.to_string()))
-            .map_err(Error::from)
+            .context(format_err!("Failed to insert header at 'category.value' of '{}'", self.get_location()))
             .context(EM::EntryHeaderWriteError)
             .map_err(Error::from)
             .map(|_| ())
@@ -84,7 +84,7 @@ impl EntryCategory for Entry {
         trace!("Has category? '{}'", self.get_location());
         self.get_header()
             .read("category.value")
-            .map_err(Error::from)
+            .context(format_err!("Failed to read header at 'category.value' of '{}'", self.get_location()))
             .context(EM::EntryHeaderReadError)
             .map_err(Error::from)
             .map(|x| x.is_some())
@@ -101,7 +101,7 @@ impl EntryCategory for Entry {
 
         self.get_header_mut()
             .delete("category.value")
-            .map_err(Error::from)
+            .context(format_err!("Failed to delete header at 'category.value' of '{}'", self.get_location()))
             .context(EM::EntryHeaderWriteError)
             .map_err(Error::from)
             .map(|_| ())
diff --git a/lib/entry/libimagentrycategory/src/iter.rs b/lib/entry/libimagentrycategory/src/iter.rs
index a16f0b9b..7ed342c7 100644
--- a/lib/entry/libimagentrycategory/src/iter.rs
+++ b/lib/entry/libimagentrycategory/src/iter.rs
@@ -20,7 +20,6 @@
 use libimagstore::storeid::StoreIdIterator;
 use libimagstore::store::Store;
 use libimagstore::store::FileLockEntry;
-use libimagerror::errors::ErrorMsg as EM;
 
 use toml_query::read::TomlValueReadTypeExt;
 
@@ -60,8 +59,8 @@ impl<'a> Iterator for CategoryNameIter<'a> {
         let query = CATEGORY_REGISTER_NAME_FIELD_PATH;
 
         while let Some(sid) = self.1.next() {
-            match sid {
-                Err(e) => return Some(Err(e).map_err(Error::from)),
+            match sid.context("Error while iterating over category names").map_err(Error::from) {
+                Err(e) => return Some(Err(e)),
                 Ok(sid) => {
                     if sid.is_in_collection(&["category"]) {
                         let func = |store: &Store| { // hack for returning Some(Result<_, _>)
@@ -70,8 +69,7 @@ impl<'a> Iterator for CategoryNameIter<'a> {
                                 .ok_or_else(|| err_msg("Store read error"))?
                                 .get_header()
                                 .read_string(query)
-                                .map_err(Error::from)
-                                .context(EM::EntryHeaderReadError)?
+                                .context(format_err!("Failed to read header at '{}'", query))?
                                 .ok_or_else(|| err_msg("Store read error"))
                                 .map_err(Error::from)
                         };
@@ -99,8 +97,8 @@ impl<'a> Iterator for CategoryEntryIterator<'a> {
 
     fn next(&mut self) -> Option<Self::Item> {
         while let Some(next) = self.1.next() {
-            match next {
-                Err(e) => return Some(Err(e).map_err(Error::from)),
+            match next.context("Error while iterating over category entries").map_err(Error::from) {
+                Err(e) => return Some(Err(e)),
                 Ok(next) => {
                     let getter = |next| -> Result<(String, FileLockEntry<'a>)> {
                         let entry = self.0
diff --git a/lib/entry/libimagentrydatetime/src/datetime.rs b/lib/entry/libimagentrydatetime/src/datetime.rs
index 611e5dbd..d7fcb828 100644
--- a/lib/entry/libimagentrydatetime/src/datetime.rs
+++ b/lib/entry/libimagentrydatetime/src/datetime.rs
@@ -92,6 +92,9 @@ impl EntryDate for Entry {
 
         self.get_header_mut()
             .insert(&DATE_HEADER_LOCATION, Value::String(date))
+            .context(format_err!("Failed to insert header '{}' in '{}'",
+                                 *DATE_HEADER_LOCATION,
+                                 self.get_location()))
             .map_err(Error::from)
             .map(|opt| opt.map(|stri| {
                 stri.as_str()
diff --git a/lib/entry/libimagentrydatetime/src/lib.rs b/lib/entry/libimagentrydatetime/src/lib.rs
index ede8b862..3e16e031 100644
--- a/lib/entry/libimagentrydatetime/src/lib.rs
+++ b/lib/entry/libimagentrydatetime/src/lib.rs
@@ -38,10 +38,10 @@
 )]
 
 #[macro_use] extern crate lazy_static;
+#[macro_use] extern crate failure;
 extern crate chrono;
 extern crate toml_query;
 extern crate toml;
-extern crate failure;
 
 extern crate libimagerror;
 extern crate libimagstore;
diff --git a/lib/entry/libimagentryedit/src/edit.rs b/lib/entry/libimagentryedit/src/edit.rs
index d6a8f59c..51ea7114 100644
--- a/lib/entry/libimagentryedit/src/edit.rs
+++ b/lib/entry/libimagentryedit/src/edit.rs
@@ -66,7 +66,9 @@ impl EditHeader for Entry {
     fn edit_header_and_content(&mut self, rt: &Runtime) -> Result<()> {
         let mut header_and_content = self.to_str()?;
         let _                      = edit_in_tmpfile(rt, &mut header_and_content)?;
-        self.replace_from_buffer(&header_and_content).map_err(Error::from)
+        self.replace_from_buffer(&header_and_content)
+            .context("Failed to replace header and content from buffer")
+            .map_err(Error::from)
     }
 
 }
diff --git a/lib/entry/libimagentryfilter/src/builtin/header/field_exists.rs b/lib/entry/libimagentryfilter/src/builtin/header/field_exists.rs
index be816c8a..674a6f08 100644
--- a/lib/entry/libimagentryfilter/src/builtin/header/field_exists.rs
+++ b/lib/entry/libimagentryfilter/src/builtin/header/field_exists.rs
@@ -23,6 +23,7 @@ use toml_query::read::TomlValueReadExt;
 use filters::failable::filter::FailableFilter;
 
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::Error;
 
 use crate::builtin::header::field_path::FieldPath;
@@ -47,6 +48,9 @@ impl FailableFilter<Entry> for FieldExists {
     fn filter(&self, e: &Entry) -> Result<bool> {
         e.get_header()
             .read(&self.header_field_path[..])
+            .context(format_err!("Failed reading header '{}' in '{}'",
+                                 self.header_field_path,
+                                 e.get_location()))
             .map_err(Error::from)
             .map(|o| o.is_some())
     }
diff --git a/lib/entry/libimagentryfilter/src/lib.rs b/lib/entry/libimagentryfilter/src/lib.rs
index 550bbf7f..71faa18b 100644
--- a/lib/entry/libimagentryfilter/src/lib.rs
+++ b/lib/entry/libimagentryfilter/src/lib.rs
@@ -40,7 +40,7 @@ extern crate regex;
 extern crate semver;
 extern crate toml;
 extern crate toml_query;
-extern crate failure;
+#[macro_use] extern crate failure;
 
 extern crate libimagstore;
 extern crate libimagentrytag;
diff --git a/lib/entry/libimagentrygps/src/entry.rs b/lib/entry/libimagentrygps/src/entry.rs
index 7c64b5c2..4bdf73be 100644
--- a/lib/entry/libimagentrygps/src/entry.rs
+++ b/lib/entry/libimagentrygps/src/entry.rs
@@ -60,11 +60,16 @@ impl GPSEntry for Entry {
         self.get_header_mut()
             .insert("gps.coordinates", c.into())
             .map(|_| ())
+            .context(format_err!("Error while inserting header 'gps.coordinates' in '{}'", self.get_location()))
             .map_err(Error::from)
     }
 
     fn get_coordinates(&self) -> Result<Option<Coordinates>> {
-        match self.get_header().read("gps.coordinates").map_err(Error::from)?  {
+        match self
+            .get_header()
+            .read("gps.coordinates")
+            .context(format_err!("Error while reading header 'gps.coordinates' in '{}'", self.get_location()))?
+        {
             Some(hdr) => Coordinates::from_value(hdr).map(Some),
             None      => Ok(None),
         }
@@ -89,7 +94,7 @@ impl GPSEntry for Entry {
         let hdr = self.get_header_mut();
         for pattern in patterns.iter() {
             let _ = hdr.delete(pattern)
-                .map_err(Error::from)
+                .context(format_err!("Error while deleting header '{}'", pattern))
                 .context("Error writing header")?;
         }
 
diff --git a/lib/entry/libimagentrygps/src/lib.rs b/lib/entry/libimagentrygps/src/lib.rs
index f819af40..8e8cade7 100644
--- a/lib/entry/libimagentrygps/src/lib.rs
+++ b/lib/entry/libimagentrygps/src/lib.rs
@@ -38,7 +38,7 @@
 extern crate toml;
 extern crate toml_query;
 #[macro_use] extern crate serde_derive;
-extern crate failure;
+#[macro_use] extern crate failure;
 
 extern crate libimagstore;
 extern crate libimagerror;
diff --git a/lib/entry/libimagentrylink/src/external.rs b/lib/entry/libimagentrylink/src/external.rs
index 3151ebe2..a31871d8 100644
--- a/lib/entry/libimagentrylink/src/external.rs
+++ b/lib/entry/libimagentrylink/src/external.rs
@@ -70,7 +70,7 @@ impl Link for Entry {
     fn get_link_uri_from_filelockentry(&self) -> Result<Option<Url>> {
         self.get_header()
             .read_string("links.external.content.url")
-            .map_err(Error::from)
+            .context(format_err!("Error reading header 'links.external.content.url' from '{}'", self.get_location()))
             .context(EM::EntryHeaderReadError)
             .map_err(Error::from)
             .and_then(|opt| match opt {
@@ -79,11 +79,13 @@ impl Link for Entry {
                     debug!("Found url, parsing: {:?}", s);
                     Url::parse(&s[..])
                         .map_err(Error::from)
+                        .context(format_err!("Failed to parse URL: '{}'", s))
                         .context(err_msg("Invalid URI"))
                         .map_err(Error::from)
                         .map(Some)
                 },
             })
+            .context("Failed to get link URI from entry")
             .map_err(Error::from)
     }
 
@@ -91,6 +93,7 @@ impl Link for Entry {
         match self.get_header().read_string("links.external.url")? {
             None        => Ok(None),
             Some(ref s) => Url::parse(&s[..])
+                .context(format_err!("Failed to parse URL: '{}'", s))
                 .map(Some)
                 .map_err(Error::from)
                 .context(EM::EntryHeaderReadError)
diff --git a/lib/entry/libimagentrylink/src/internal.rs b/lib/entry/libimagentrylink/src/internal.rs
index 2ed5e5f6..224eac99 100644
--- a/lib/entry/libimagentrylink/src/internal.rs
+++ b/lib/entry/libimagentrylink/src/internal.rs
@@ -265,7 +265,7 @@ impl InternalLinker for Entry {
         let res = self
             .get_header()
             .read("links.internal")
-            .map_err(Error::from)
+            .context(format_err!("Failed to read header 'links.internal' of '{}'", self.get_location()))
             .context(EM::EntryHeaderReadError)
             .context(EM::EntryHeaderError)
             .map_err(Error::from)
@@ -299,7 +299,7 @@ impl InternalLinker for Entry {
         let res = self
             .get_header_mut()
             .insert("links.internal", Value::Array(new_links))
-            .map_err(Error::from)
+            .context(format_err!("Failed to insert header 'links.internal' of '{}'", self.get_location()))
             .context(EM::EntryHeaderReadError)
             .map_err(Error::from);
         process_rw_result(res)
@@ -336,7 +336,7 @@ impl InternalLinker for Entry {
 
     fn unlink(&mut self, store: &Store) -> Result<()> {
         for id in self.get_internal_links()?.map(|l| l.get_store_id().clone()) {
-            match store.get(id).map_err(Error::from)? {
+            match store.get(id).context("Failed to get entry")? {
                 Some(mut entry) => self.remove_internal_link(&mut entry)?,
                 None            => return Err(err_msg("Link target does not exist")),
             }
@@ -382,7 +382,7 @@ fn rewrite_links<I: Iterator<Item = Link>>(header: &mut Value, links: I) -> Resu
     debug!("Setting new link array: {:?}", links);
     let process = header
         .insert("links.internal", Value::Array(links))
-        .map_err(Error::from)
+        .context(format_err!("Failed to insert header 'links.internal'"))
         .context(EM::EntryHeaderReadError)
         .map_err(Error::from);
     process_rw_result(process).map(|_| ())
@@ -409,7 +409,7 @@ fn add_foreign_link(target: &mut Entry, from: StoreId) -> Result<()> {
             let res = target
                 .get_header_mut()
                 .insert("links.internal", Value::Array(links))
-                .map_err(Error::from)
+                .context(format_err!("Failed to insert header 'links.internal'"))
                 .context(EM::EntryHeaderReadError)
                 .map_err(Error::from);
 
diff --git a/lib/entry/libimagentryref/src/reference.rs b/lib/entry/libimagentryref/src/reference.rs
index 729d23ef..2f7aa353 100644
--- a/lib/entry/libimagentryref/src/reference.rs
+++ b/lib/entry/libimagentryref/src/reference.rs
@@ -89,6 +89,7 @@ pub mod fassade {
     use libimagentryutil::isa::Is;
 
     use failure::Fallible as Result;
+    use failure::ResultExt;
     use failure::Error;
 
     use crate::hasher::sha1::Sha1Hasher;
@@ -104,7 +105,7 @@ pub mod fassade {
     impl RefFassade for Entry {
         /// Check whether the underlying object is actually a ref
         fn is_ref(&self) -> Result<bool> {
-            self.is::<IsRef>().map_err(Error::from)
+            self.is::<IsRef>().context("Failed to check is-ref flag").map_err(Error::from)
         }
 
         fn as_ref_with_hasher<H: Hasher>(&self)     -> RefWithHasher<H> {
@@ -163,7 +164,7 @@ impl<'a, H: Hasher> Ref for RefWithHasher<'a, H> {
 
     /// Check whether the underlying object is actually a ref
     fn is_ref(&self) -> Result<bool> {
-        self.0.is::<IsRef>().map_err(Error::from)
+        self.0.is::<IsRef>().context("Failed to check is-ref flag").map_err(Error::from)
     }
 
     fn get_hash(&self) -> Result<&str> {
@@ -171,6 +172,7 @@ impl<'a, H: Hasher> Ref for RefWithHasher<'a, H> {
         self.0
             .get_header()
             .read(&header_path)
+            .context(format_err!("Failed to read header at '{}'", header_path))
             .map_err(Error::from)?
             .ok_or_else(|| {
                 Error::from(EM::EntryHeaderFieldMissing("ref.hash.<hash>"))
@@ -210,7 +212,7 @@ impl<'a, H: Hasher> Ref for RefWithHasher<'a, H> {
         self.0
             .get_header()
             .read("ref.relpath")
-            .map_err(Error::from)?
+            .context("Failed to read header at 'ref.relpath'")?
             .ok_or_else(|| Error::from(EM::EntryHeaderFieldMissing("ref.relpath")))
             .and_then(|v| {
                 v.as_str()
@@ -223,19 +225,20 @@ impl<'a, H: Hasher> Ref for RefWithHasher<'a, H> {
     fn hash_valid(&self, config: &Config) -> Result<bool> {
         let ref_header = self.0
             .get_header()
-            .read("ref")?
+            .read("ref")
+            .context("Failed to read header at 'ref'")?
             .ok_or_else(|| err_msg("Header missing at 'ref'"))?;
 
         let basepath_name = ref_header
             .read("basepath")
-            .map_err(Error::from)?
+            .context("Failed to read header at 'ref.basepath'")?
             .ok_or_else(|| err_msg("Header missing at 'ref.basepath'"))?
             .as_str()
             .ok_or_else(|| Error::from(EM::EntryHeaderTypeError2("ref.hash.<hash>", "string")))?;
 
         let path = ref_header
             .read("relpath")
-            .map_err(Error::from)?
+            .context("Failed to read header at 'ref.relpath'")?
             .ok_or_else(|| err_msg("Header missing at 'ref.relpath'"))?
             .as_str()
             .map(PathBuf::from)
@@ -246,7 +249,7 @@ impl<'a, H: Hasher> Ref for RefWithHasher<'a, H> {
 
         ref_header
             .read(H::NAME)
-            .map_err(Error::from)?
+            .context(format_err!("Failed to read header at 'ref.{}'", H::NAME))?
             .ok_or_else(|| format_err!("Header missing at 'ref.{}'", H::NAME))
             .and_then(|v| {
                 v.as_str().ok_or_else(|| {
@@ -352,7 +355,9 @@ impl<'a, H> MutRef for MutRefWithHasher<'a, H>
                 trace!("Using relpath = {} to make header section", relpath.display());
                 make_header_section(hash, H::NAME, relpath, basepath_name)
             })
-            .and_then(|h| self.0.get_header_mut().insert("ref", h).map_err(Error::from))
+            .and_then(|h| self.0.get_header_mut().insert("ref", h)
+                      .context("Failed to insert 'ref' in header")
+                      .map_err(Error::from))
             .and_then(|_| self.0.set_isflag::<IsRef>())
             .context("Making ref out of entry")?;
 
diff --git a/lib/entry/libimagentrytag/src/tagable.rs b/lib/entry/libimagentrytag/src/tagable.rs
index 6ff5e4cc..196b3f0d 100644
--- a/lib/entry/libimagentrytag/src/tagable.rs
+++ b/lib/entry/libimagentrytag/src/tagable.rs
@@ -51,6 +51,7 @@ impl Tagable for Value {
 
     fn get_tags(&self) -> Result<Vec<Tag>> {
         self.read("tag.values")
+            .context(format_err!("Failed to read header at 'tag.values'"))
             .map_err(Error::from)
             .context(EM::EntryHeaderReadError)?
             .map(|val| {
diff --git a/lib/entry/libimagentryutil/src/isa.rs b/lib/entry/libimagentryutil/src/isa.rs
index f10152b8..7730eea2 100644
--- a/lib/entry/libimagentryutil/src/isa.rs
+++ b/lib/entry/libimagentryutil/src/isa.rs
@@ -18,6 +18,7 @@
 //
 
 use failure::Fallible as Result;
+use failure::ResultExt;
 use failure::Error;
 
 use toml::Value;
@@ -79,7 +80,12 @@ impl Is for ::libimagstore::store::Entry {
     fn is<T: IsKindHeaderPathProvider>(&self) -> Result<bool> {
         let field = T::kindflag_header_location();
 
-        match self.get_header().read_bool(field).map_err(Error::from)? {
+        match self
+            .get_header()
+            .read_bool(field)
+            .context(format_err!("Failed reading header '{}' in '{}'", field, self.get_location()))
+            .map_err(Error::from)?
+        {
             Some(b) => Ok(b),
             None    => Ok(false),
         }
@@ -88,6 +94,7 @@ impl Is for ::libimagstore::store::Entry {
     fn set_isflag<T: IsKindHeaderPathProvider>(&mut self) -> Result<()> {
         self.get_header_mut()
             .insert(T::kindflag_header_location(), Value::Boolean(true))
+            .context(format_err!("Failed inserting header '{}' in '{}'", T::kindflag_header_location(), self.get_location()))
             .map_err(Error::from)
             .map(|_| ())
     }
@@ -96,6 +103,7 @@ impl Is for ::libimagstore::store::Entry {
         trace!("Trying to remove: {}", T::kindflag_header_location());
         self.get_header_mut()
             .delete(T::kindflag_header_location())
+            .context(format_err!("Failed deleting header '{}' in '{}'", T::kindflag_header_location(), self.get_location()))
             .map_err(Error::from)
             .map(|_| ())
     }
diff --git a/lib/entry/libimagentryutil/src/lib.rs b/lib/entry/libimagentryutil/src/lib.rs
index 6dbc1870..c5feb7cb 100644
--- a/lib/entry/libimagentryutil/src/lib.rs
+++ b/lib/entry/libimagentryutil/src/lib.rs
@@ -40,7 +40,7 @@
 extern crate filters;
 extern crate toml;
 extern crate toml_query;
-extern crate failure;
+#[macro_use] extern crate failure;
 #[macro_use] extern crate log;
 
 extern crate libimagstore;
diff --git a/lib/entry/libimagentryview/src/builtin/editor.rs b/lib/entry/libimagentryview/src/builtin/editor.rs
index 8a702e63..35845649 100644
--- a/lib/entry/libimagentryview/src/builtin/editor.rs
+++ b/lib/entry/libimagentryview/src/builtin/editor.rs
@@ -27,7 +27,6 @@ use crate::viewer::Viewer;
 use failure::Fallible as Result;
 use failure::ResultExt;
 use failure::Error;
-use failure::err_msg;
 
 pub struct EditorView<'a>(&'a Runtime<'a>);
 
@@ -43,7 +42,7 @@ impl<'a> Viewer for EditorView<'a> {
     {
         let mut entry = e.to_str()?.clone().to_string();
         edit_in_tmpfile(self.0, &mut entry)
-            .context(err_msg("Error while viewing"))
+            .context("Error while viewing")
             .map_err(Error::from)
     }
 }
diff --git a/lib/etc/libimaginteraction/src/ask.rs b/lib/etc/libimaginteraction/src/ask.rs
index 56a411e1..ea112d7c 100644
--- a/lib/etc/libimaginteraction/src/ask.rs
+++ b/lib/etc/libimaginteraction/src/ask.rs
@@ -178,10 +178,12 @@ pub fn ask_select_from_list(list: &[&str]) -> Result<String> {
 /// The `nl` parameter can be used to configure whether a newline character should be printed
 pub fn ask_question(question: &str, nl: bool, output: &mut Write) -> Result<()> {
     if nl {
-        writeln!(output, "[imag]: {}?", Yellow.paint(question)).map_err(Error::from)
+        writeln!(output, "[imag]: {}?", Yellow.paint(question))
     } else {
-        write!(output, "[imag]: {}?", Yellow.paint(question)).map_err(Error::from)
+        write!(output, "[imag]: {}?", Yellow.paint(question))
     }
+    .context("Failed to write question to output")
+    .map_err(Error::from)
 }
 
 #[cfg(test)]