diff --git a/dev/breeze/src/airflow_breeze/commands/ci_image_commands.py b/dev/breeze/src/airflow_breeze/commands/ci_image_commands.py
index 1329ba607c4e4..020cd30698a6a 100644
--- a/dev/breeze/src/airflow_breeze/commands/ci_image_commands.py
+++ b/dev/breeze/src/airflow_breeze/commands/ci_image_commands.py
@@ -383,17 +383,21 @@ def should_we_run_the_build(build_ci_params: BuildCiParams, verbose: bool) -> bo
         return False
     try:
         answer = user_confirm(
-            message="Do you want to build the image?", timeout=STANDARD_TIMEOUT, default_answer=Answer.NO
+            message="Do you want to build the image (this works best when you have good connection and "
+            "can take usually from 20 seconds to few minutes depending how old your image is)?",
+            timeout=STANDARD_TIMEOUT,
+            default_answer=Answer.NO,
         )
         if answer == answer.YES:
             if is_repo_rebased(build_ci_params.github_repository, build_ci_params.airflow_branch):
                 return True
             else:
                 get_console().print(
-                    "\n[warning]This might take a lot of time, we think you should rebase first.[/]\n"
+                    "\n[warning]This might take a lot of time (more than 10 minutes) even if you have"
+                    "a good network connection. We think you should attempt to rebase first.[/]\n"
                 )
                 answer = user_confirm(
-                    "But if you really, really want - you can do it. Are you really sure?",
+                    "But if you really, really want - you can attempt it. Are you really sure?",
                     timeout=STANDARD_TIMEOUT,
                     default_answer=Answer.NO,
                 )
@@ -401,8 +405,8 @@ def should_we_run_the_build(build_ci_params: BuildCiParams, verbose: bool) -> bo
                     return True
                 else:
                     get_console().print(
-                        "[info]Please rebase your code before continuing.[/]\n"
-                        "Check this link to know more "
+                        f"[info]Please rebase your code to latest {build_ci_params.airflow_branch} "
+                        "before continuing.[/]\nCheck this link to find out how "
                         "https://github.com/apache/airflow/blob/main/CONTRIBUTING.rst#id15\n"
                     )
                     get_console().print('[error]Exiting the process[/]\n')
@@ -538,6 +542,9 @@ def rebuild_ci_image_if_needed(
         if verbose:
             get_console().print(f'[info]{build_params.image_type} image already built locally.[/]')
     else:
-        get_console().print(f'[warning]{build_params.image_type} image not built locally. Forcing build.[/]')
+        get_console().print(
+            f'[warning]{build_params.image_type} image was never built locally or deleted. '
+            'Forcing build.[/]'
+        )
         ci_image_params.force_build = True
     build_ci_image(verbose, dry_run=dry_run, ci_image_params=ci_image_params)
diff --git a/dev/breeze/src/airflow_breeze/utils/reinstall.py b/dev/breeze/src/airflow_breeze/utils/reinstall.py
index 0df3a6a0eaa05..e58ac2c731160 100644
--- a/dev/breeze/src/airflow_breeze/utils/reinstall.py
+++ b/dev/breeze/src/airflow_breeze/utils/reinstall.py
@@ -50,7 +50,8 @@ def ask_to_reinstall_breeze(breeze_sources: Path, timeout: Optional[int] = STAND
          otherwise it is yes
     """
     answer = user_confirm(
-        f"Do you want to reinstall Breeze from {breeze_sources.parent.parent}?",
+        f"Do you want to reinstall Breeze from {breeze_sources.parent.parent} "
+        "(This should usually take couple of seconds)?",
         default_answer=Answer.NO if timeout else Answer.YES,
         timeout=timeout,
     )
@@ -77,7 +78,8 @@ def warn_different_location(installation_airflow_sources: Path, current_airflow_
         f"Current Airflow sources : {current_airflow_sources}\n\n"
         f"[warning]This might cause various problems!![/]\n\n"
         f"If you experience problems - reinstall Breeze with:\n\n"
-        f"    {NAME} self-upgrade --force --use-current-airflow-sources\n\n"
+        f"    {NAME} self-upgrade --force --use-current-airflow-sources\n"
+        f"\nThis should usually take couple of seconds.\n"
     )
 
 
@@ -86,5 +88,6 @@ def warn_dependencies_changed():
         f"\n[warning]Breeze dependencies changed since the installation![/]\n\n"
         f"[warning]This might cause various problems!![/]\n\n"
         f"If you experience problems - reinstall Breeze with:\n\n"
-        f"    {NAME} self-upgrade --force\n\n"
+        f"    {NAME} self-upgrade --force\n"
+        "\nThis should usually take couple of seconds.\n"
     )