I have TB 68.5.0. One of my gmail accounts refuses to send out emails. I checked settings, which seem to be ok just as other gmail accounts that are working .
See attached screen shots. I have other gmail accounts in TB and they are working fine.
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I'd suggest to start a new topic for this.
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Set the 'Authentication method' for the SMTP server to 'OAuth2'. You'll be prompted for your Gmail password the next time you attempt to send a message, and you'll have to allow Thunderbird to access your Gmail account.
I did as you suggested. When I tried to send out a mail, it did not ask for the PW; it simply failed. See attached file.
Please post your Troubleshooting Information.
At the top right of the Thunderbird window, click the menu button 
, then select Help > Troubleshooting Information.
Press the "Copy text to clipboard button" and paste the information into your reply.
Application Basics
Name: Thunderbird Version: 68.5.0 Build ID: 20200210021033
Update Channel: release User Agent: Mozilla/5.0 (Windows NT 10.0; WOW64; rv:68.0) Gecko/20100101 Firefox/68.0 Thunderbird/68.5.0 OS: Windows_NT 10.0
Launcher Process: Enabled
Multiprocess Windows: 0/0
Disabled
Remote Processes: 0
Enterprise Policies: Inactive
Google Location Service Key: Missing
Google Safebrowsing Key: Missing
Mozilla Location Service Key: Missing
Safe Mode: false
Mail and News Accounts
account2:
INCOMING: account2, , (none) Local Folders, plain, passwordCleartext
account3:
INCOMING: account3, , (imap) imap.gmail.com:993, SSL, passwordCleartext
OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true
account4:
INCOMING: account4, , (imap) mail.takashinaarchitect.com:143, plain, passwordCleartext
OUTGOING: , mail.takashinaarchitect.com:25, plain, passwordCleartext, true
account5:
INCOMING: account5, , (imap) mail.takashinaarchitect.com:143, plain, passwordCleartext
OUTGOING: , mail.takashinaarchitect.com:25, plain, passwordCleartext, true
account6:
INCOMING: account6, , (imap) mail.takashinaarchitect.com:143, plain, passwordCleartext
OUTGOING: , mail.takashinaarchitect.com:25, plain, passwordCleartext, true
account7:
INCOMING: account7, , (imap) mail.takashinaarchitect.com:143, plain, passwordCleartext
OUTGOING: , mail.takashinaarchitect.com:25, plain, passwordCleartext, true
account8:
INCOMING: account8, , (imap) mtarch.ipage.com:143, alwaysSTARTTLS, passwordCleartext
OUTGOING: , mtarch.ipage.com:587, plain, passwordCleartext, true
account9:
INCOMING: account9, , (imap) mtarch.ipage.com:143, alwaysSTARTTLS, passwordCleartext
OUTGOING: , mtarch.ipage.com:587, plain, passwordCleartext, true
account10:
INCOMING: account10, , (imap) mtarch.ipage.com:143, alwaysSTARTTLS, passwordCleartext
OUTGOING: , mtarch.ipage.com:587, plain, passwordCleartext, true
account11:
INCOMING: account11, , (imap) imap.googlemail.com:993, SSL, passwordCleartext
OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true
account12:
INCOMING: account12, , (imap) imap.gmail.com:993, SSL, OAuth2
OUTGOING: , smtp.gmail.com:465, SSL, OAuth2, true
account13:
INCOMING: account13, , (imap) imap.googlemail.com:993, SSL, OAuth2
OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true
account14:
INCOMING: account14, , (imap) imap.gmail.com:993, SSL, OAuth2
OUTGOING: , smtp.gmail.com:465, SSL, OAuth2, true
account15:
INCOMING: account15, , (imap) imap.gmail.com:993, SSL, OAuth2
OUTGOING: , smtp.gmail.com:465, SSL, OAuth2, true
Crash Reports for the Last 3 Days
Remote Processes
Type: Count
Extensions
Name
Version
Enabled
ID
Amazon.com 1.1 true amazondotcom@search.mozilla.org
Bing
1.0
true
bing@search.mozilla.org
DuckDuckGo
1.0
true
ddg@search.mozilla.org
gContactSync
3.1.7
true
gContactSync@pirules.net
Google
1.0
true
google@search.mozilla.org
Lightning
68.5.0
true
{e2fda1a4-762b-4020-b5ad-a41df1933103}
Manually sort folders
2.0.2
true
tbsortfolders@xulforum.org
Send Later
7.4.0
true
sendlater3@kamens.us
Twitter
1.0
true
twitter@search.mozilla.org
Wikipedia (en)
1.0
true
wikipedia@search.mozilla.org
ImportExportTools
3.3.2
false
{3ed8cc52-86fc-4613-9026-c1ef969da4c3}
Security Software
Type: Name
Antivirus: Avast Antivirus
Antispyware:
Firewall: Windows Firewall
Graphics
Features
Compositing: Basic
Asynchronous Pan/Zoom: none
WebGL 1 Driver WSI Info: EGL_VENDOR: Google Inc. (adapter LUID: 000000000000fbb9)
EGL_VERSION: 1.4 (ANGLE 2.1.0.8a050090f926) EGL_EXTENSIONS: EGL_EXT_create_context_robustness EGL_ANGLE_d3d_share_handle_client_buffer EGL_ANGLE_d3d_texture_client_buffer EGL_ANGLE_surface_d3d_texture_2d_share_handle EGL_ANGLE_query_surface_pointer EGL_ANGLE_window_fixed_size EGL_ANGLE_keyed_mutex EGL_ANGLE_surface_orientation EGL_ANGLE_direct_composition EGL_NV_post_sub_buffer EGL_KHR_create_context EGL_EXT_device_query EGL_KHR_image EGL_KHR_image_base EGL_KHR_gl_texture_2D_image EGL_KHR_gl_texture_cubemap_image EGL_KHR_gl_renderbuffer_image EGL_KHR_get_all_proc_addresses EGL_KHR_stream EGL_KHR_stream_consumer_gltexture EGL_NV_stream_consumer_gltexture_yuv EGL_ANGLE_flexible_surface_compatibility EGL_ANGLE_stream_producer_d3d_texture EGL_ANGLE_create_context_webgl_compatibility EGL_CHROMIUM_create_context_bind_generates_resource EGL_CHROMIUM_sync_control EGL_EXT_pixel_format_float EGL_KHR_surfaceless_context EGL_ANGLE_display_texture_share_group EGL_ANGLE_create_context_client_arrays EGL_ANGLE_program_cache_control EGL_ANGLE_robust_resource_initialization EGL_ANGLE_create_context_extensions_enabled EGL_ANDROID_blob_cache EGL_ANDROID_recordable EGL_EXTENSIONS(nullptr): EGL_EXT_client_extensions EGL_EXT_platform_base EGL_EXT_platform_device EGL_ANGLE_platform_angle EGL_ANGLE_platform_angle_d3d EGL_ANGLE_device_creation EGL_ANGLE_device_creation_d3d11 EGL_ANGLE_experimental_present_path EGL_KHR_client_get_all_proc_addresses EGL_KHR_debug EGL_ANGLE_explicit_context
WebGL 1 Driver Renderer: Google Inc. -- ANGLE (Intel(R) HD Graphics 530 Direct3D11 vs_5_0 ps_5_0)
WebGL 1 Driver Version: OpenGL ES 2.0 (ANGLE 2.1.0.8a050090f926)
WebGL 1 Driver Extensions: GL_ANGLE_client_arrays GL_ANGLE_depth_texture GL_ANGLE_explicit_context GL_ANGLE_explicit_context_gles1 GL_ANGLE_framebuffer_blit GL_ANGLE_framebuffer_multisample GL_ANGLE_instanced_arrays GL_ANGLE_lossy_etc_decode GL_ANGLE_memory_size GL_ANGLE_multi_draw GL_ANGLE_multiview_multisample GL_ANGLE_pack_reverse_row_order GL_ANGLE_program_cache_control GL_ANGLE_provoking_vertex GL_ANGLE_request_extension GL_ANGLE_robust_client_memory GL_ANGLE_texture_compression_dxt3 GL_ANGLE_texture_compression_dxt5 GL_ANGLE_texture_usage GL_ANGLE_translated_shader_source GL_CHROMIUM_bind_generates_resource GL_CHROMIUM_bind_uniform_location GL_CHROMIUM_color_buffer_float_rgb GL_CHROMIUM_color_buffer_float_rgba GL_CHROMIUM_copy_compressed_texture GL_CHROMIUM_copy_texture GL_CHROMIUM_sync_query GL_EXT_blend_func_extended GL_EXT_blend_minmax GL_EXT_color_buffer_half_float GL_EXT_debug_marker GL_EXT_discard_framebuffer GL_EXT_disjoint_timer_query GL_EXT_draw_buffers GL_EXT_float_blend GL_EXT_frag_depth GL_EXT_instanced_arrays GL_EXT_map_buffer_range GL_EXT_occlusion_query_boolean GL_EXT_read_format_bgra GL_EXT_robustness GL_EXT_sRGB GL_EXT_shader_texture_lod GL_EXT_texture_compression_bptc GL_EXT_texture_compression_dxt1 GL_EXT_texture_compression_s3tc_srgb GL_EXT_texture_filter_anisotropic GL_EXT_texture_format_BGRA8888 GL_EXT_texture_rg GL_EXT_texture_storage GL_EXT_unpack_subimage GL_KHR_debug GL_KHR_parallel_shader_compile GL_KHR_robust_buffer_access_behavior GL_NV_EGL_stream_consumer_external GL_NV_fence GL_NV_pack_subimage GL_NV_pixel_buffer_object GL_OES_EGL_image GL_OES_EGL_image_external GL_OES_compressed_ETC1_RGB8_texture GL_OES_depth32 GL_OES_element_index_uint GL_OES_get_program_binary GL_OES_mapbuffer GL_OES_packed_depth_stencil GL_OES_rgb8_rgba8 GL_OES_standard_derivatives GL_OES_surfaceless_context GL_OES_texture_border_clamp GL_OES_texture_float GL_OES_texture_float_linear GL_OES_texture_half_float GL_OES_texture_half_float_linear GL_OES_texture_npot GL_OES_vertex_array_object OES_compressed_EAC_R11_signed_texture OES_compressed_EAC_R11_unsigned_texture OES_compressed_EAC_RG11_signed_texture OES_compressed_EAC_RG11_unsigned_texture OES_compressed_ETC2_RGB8_texture OES_compressed_ETC2_RGBA8_texture OES_compressed_ETC2_punchthroughA_RGBA8_texture OES_compressed_ETC2_punchthroughA_sRGB8_alpha_texture OES_compressed_ETC2_sRGB8_alpha8_texture OES_compressed_ETC2_sRGB8_texture
WebGL 1 Extensions: ANGLE_instanced_arrays EXT_blend_minmax EXT_color_buffer_half_float EXT_disjoint_timer_query EXT_float_blend EXT_frag_depth EXT_shader_texture_lod EXT_sRGB EXT_texture_compression_bptc EXT_texture_filter_anisotropic OES_element_index_uint OES_standard_derivatives OES_texture_float OES_texture_float_linear OES_texture_half_float OES_texture_half_float_linear OES_vertex_array_object WEBGL_color_buffer_float WEBGL_compressed_texture_s3tc WEBGL_compressed_texture_s3tc_srgb WEBGL_debug_renderer_info WEBGL_debug_shaders WEBGL_depth_texture WEBGL_draw_buffers WEBGL_lose_context
WebGL 2 Driver WSI Info: EGL_VENDOR: Google Inc. (adapter LUID: 000000000000fbb9)
EGL_VERSION: 1.4 (ANGLE 2.1.0.8a050090f926) EGL_EXTENSIONS: EGL_EXT_create_context_robustness EGL_ANGLE_d3d_share_handle_client_buffer EGL_ANGLE_d3d_texture_client_buffer EGL_ANGLE_surface_d3d_texture_2d_share_handle EGL_ANGLE_query_surface_pointer EGL_ANGLE_window_fixed_size EGL_ANGLE_keyed_mutex EGL_ANGLE_surface_orientation EGL_ANGLE_direct_composition EGL_NV_post_sub_buffer EGL_KHR_create_context EGL_EXT_device_query EGL_KHR_image EGL_KHR_image_base EGL_KHR_gl_texture_2D_image EGL_KHR_gl_texture_cubemap_image EGL_KHR_gl_renderbuffer_image EGL_KHR_get_all_proc_addresses EGL_KHR_stream EGL_KHR_stream_consumer_gltexture EGL_NV_stream_consumer_gltexture_yuv EGL_ANGLE_flexible_surface_compatibility EGL_ANGLE_stream_producer_d3d_texture EGL_ANGLE_create_context_webgl_compatibility EGL_CHROMIUM_create_context_bind_generates_resource EGL_CHROMIUM_sync_control EGL_EXT_pixel_format_float EGL_KHR_surfaceless_context EGL_ANGLE_display_texture_share_group EGL_ANGLE_create_context_client_a
I divided the text bec it was too long.
Antivirus: Avast Antivirus
Avast is known to be problematic in many ways, and I wouldn't use it at all.
Follow these instructions and disable the interception of secure connections in Avast. https://support.mozilla.org/en-US/kb/error-codes-secure-websites#w_avastavg
Upravil uživatel christ1 dne
I unchecked the box at Avast. I tried to send an email. TB tried to send out for a while and failed. See attached.
From your Troubleshooting Information, there are 6 Gmail accounts. Which is the one with the problem?
Are there problems with any of the other Gmail accounts? If so, which ones?
Problem account is: japaneselinguist1@gmail.com. No other gmail accounts have shown this problem.
When you change the authentication method, it's a good idea to delete the account passwords from Tools/Options/Security/Passwords/Saved Passwords, restart TB, and enter the password when prompted. For OAuth to work, cookies must be enabled in TB Tools/Options/Privacy.
Can you match it to the ones listed in the Troubleshooting Information, so one of account3, account11, account12, account13, account14, account15?
The point is, some of those already do have OAuth2 authentication set, while others don't.
I made all gmail accounts to OAuth2 authentication and tried to send out a mail. The same as before: Timeout message.
Try to start Windows in safe mode with networking enabled. - Win10 https://support.microsoft.com/en-us/help/12376/windows-10-start-your-pc-in-safe-mode
Does the problem go away?
When I tried to boot in to Safe Mode, Windows asks for the PW, which I do not remember. Is it something printed on the installation CD? I use PIN to log in normally id not Safe Mode.
Now, none of gmail accounts allow email to go out. "Timeout" message appears for all cases.
When I tried to boot in to Safe Mode, Windows asks for the PW, which I do not remember.
Unfortunately I can't help with that.
Is it something printed on the installation CD?
No, it's something you or an admin has set at some point.
Windows safe mode would be important to test to rule out (or confirm) Avast is still causing problems.
Then, if I uninstall Avast, that would do the test without safe-mode, right?
Not exactly. When uninstalling Avast, Windows Defender will automatically kick in. You'd need to create an exception for the Thunderbird profile folder in Windows Defender. For the location of the Thunderbird profile see https://support.mozilla.org/kb/profiles-where-thunderbird-stores-user-data
On the other hand, getting rid of Avast sounds like a good idea, so just give it a try.
Uninstalled Avast. (Is Windows enough to protect?)
How to create an exception in Windows Defender?