diff --git a/cli/src/action/delete.rs b/cli/src/action/delete.rs
index 52b093e..fc0538b 100644
--- a/cli/src/action/delete.rs
+++ b/cli/src/action/delete.rs
@@ -1,4 +1,5 @@
 use clap::ArgMatches;
+use failure::Fail;
 use ffsend_api::action::delete::{
     Error as DeleteError,
     Delete as ApiDelete,
@@ -15,7 +16,8 @@ use cmd::matcher::{
     main::MainMatcher,
 };
 use error::ActionError;
-use util::{ensure_owner_token, print_success};
+use history::History;
+use util::{ensure_owner_token, print_error, print_success};
 
 /// A file delete action.
 pub struct Delete<'a> {
@@ -52,6 +54,17 @@ impl<'a> Delete<'a> {
         // Send the file deletion request
         ApiDelete::new(&file, None).invoke(&client)?;
 
+        // Remove the file from the history manager
+        // TODO: also remove if it was expired
+        if let Err(err) = History::load_remove_save(
+            matcher_main.history(),
+            &file,
+        ) {
+            print_error(err.context(
+                "Failed to remove file from local history, ignoring",
+            ));
+        }
+
         // Print a success message
         print_success("File deleted");
 
diff --git a/cli/src/action/exists.rs b/cli/src/action/exists.rs
index 8422817..854a035 100644
--- a/cli/src/action/exists.rs
+++ b/cli/src/action/exists.rs
@@ -1,4 +1,5 @@
 use clap::ArgMatches;
+use failure::Fail;
 use ffsend_api::action::exists::{
     Error as ExistsError,
     Exists as ApiExists,
@@ -12,8 +13,11 @@ use ffsend_api::reqwest::Client;
 use cmd::matcher::{
     Matcher,
     exists::ExistsMatcher,
+    main::MainMatcher,
 };
 use error::ActionError;
+use history::History;
+use util::print_error;
 
 /// A file exists action.
 pub struct Exists<'a> {
@@ -33,6 +37,7 @@ impl<'a> Exists<'a> {
     pub fn invoke(&self) -> Result<(), ActionError> {
         // Create the command matchers
         let matcher_exists = ExistsMatcher::with(self.cmd_matches).unwrap();
+        let matcher_main = MainMatcher::with(self.cmd_matches).unwrap();
 
         // Get the share URL
         let url = matcher_exists.url();
@@ -54,6 +59,19 @@ impl<'a> Exists<'a> {
             println!("Password: {:?}", exists_response.has_password());
         }
 
+        // Remove the file from the history manager if it doesn't exist
+        // TODO: add if it does exist
+        if !exists {
+            if let Err(err) = History::load_remove_save(
+                matcher_main.history(),
+                &file,
+            ) {
+                print_error(err.context(
+                    "Failed to remove file from local history, ignoring",
+                ));
+            }
+        }
+
         Ok(())
     }
 }
diff --git a/cli/src/action/info.rs b/cli/src/action/info.rs
index a6df14f..e0de85d 100644
--- a/cli/src/action/info.rs
+++ b/cli/src/action/info.rs
@@ -20,6 +20,7 @@ use cmd::matcher::{
     info::InfoMatcher,
     main::MainMatcher,
 };
+use history::History;
 use util::{ensure_owner_token, ensure_password, print_error};
 
 /// A file info action.
@@ -58,6 +59,16 @@ impl<'a> Info<'a> {
         // Check whether the file exists
         let exists = ApiExists::new(&file).invoke(&client)?;
         if !exists.exists() {
+            // Remove the file from the history manager if it doesn't exist
+            if let Err(err) = History::load_remove_save(
+                matcher_main.history(),
+                &file,
+            ) {
+                print_error(err.context(
+                    "Failed to remove file from local history, ignoring",
+                ));
+            }
+
             return Err(Error::Expired);
         }
 
diff --git a/cli/src/action/upload.rs b/cli/src/action/upload.rs
index 62dfd14..f4bf6fc 100644
--- a/cli/src/action/upload.rs
+++ b/cli/src/action/upload.rs
@@ -130,7 +130,9 @@ impl<'a> Upload<'a> {
             matcher_main.history(),
             file.clone(),
         ) {
-            print_error(err.context("Failed to add file to history, ignoring"));
+            print_error(err.context(
+                "Failed to add file to local history, ignoring",
+            ));
         }
 
         // Open the URL in the browser
diff --git a/cli/src/history.rs b/cli/src/history.rs
index cf852e6..51c009d 100644
--- a/cli/src/history.rs
+++ b/cli/src/history.rs
@@ -111,14 +111,23 @@ impl History {
 
     /// Load the history from the given path, add the given file, and save it
     /// again.
-    /// If there is not history file at the given path, a new empty one will
-    /// be created.
+    /// If there is no file at the given path, new history will be created.
     pub fn load_add_save(path: PathBuf, file: RemoteFile) -> Result<(), Error> {
         let mut history = Self::load_or_new(path)?;
         history.add(file);
         history.save().map_err(|err| err.into())
     }
 
+    /// Load the history from the given path, remove the given file by it's
+    /// ID, and save it again.
+    /// True is returned if any file was removed.
+    pub fn load_remove_save(path: PathBuf, file: &RemoteFile) -> Result<bool, Error> {
+        let mut history = Self::load_or_new(path)?;
+        let removed = history.remove(file);
+        history.save()?;
+        Ok(removed)
+    }
+
     /// Add the given remote file to the history.
     pub fn add(&mut self, file: RemoteFile) {
         self.files.push(file);